#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/53/2225375.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_2225375
loop_
_publ_author_name
'Naveenkumar, H. S.'
'Sadikun, Amirin'
'Ibrahim, Pazilah'
'Yeap, Chin Sing'
'Fun, Hoong-Kun'
_publ_section_title
;
 (E)-N'-(2,4,5-Trifluorobenzylidene)isonicotinohydrazide
 monohydrate
;
_journal_coeditor_code           SJ2725
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o579
_journal_paper_doi               10.1107/S1600536810004514
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H8 F3 N3 O, H2 O'
_chemical_formula_moiety         'C13 H8 F3 N3 O, H2 O'
_chemical_formula_sum            'C13 H10 F3 N3 O2'
_chemical_formula_weight         297.24
_chemical_name_systematic
;
(E)-N'-(2,4,5-Trifluorobenzylidene)isonicotinohydrazide
monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.6160(10)
_cell_angle_beta                 86.5560(10)
_cell_angle_gamma                76.0560(10)
_cell_formula_units_Z            2
_cell_length_a                   4.92410(10)
_cell_length_b                   6.39150(10)
_cell_length_c                   21.3387(2)
_cell_measurement_reflns_used    6031
_cell_measurement_temperature    296
_cell_measurement_theta_max      30.80
_cell_measurement_theta_min      2.87
_cell_volume                     650.580(18)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14710
_diffrn_reflns_theta_full        30.81
_diffrn_reflns_theta_max         30.81
_diffrn_reflns_theta_min         2.87
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.9835
_exptl_absorpt_correction_T_min  0.9584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0764P)²+0.0515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1464
_reflns_number_gt                2730
_reflns_number_total             4024
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2725.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2225375
_cod_database_fobs_code          2225375
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
F F1 1.20930(18) 0.63383(14) 0.34682(4) 0.0667(3) Uani d . 1 . .
F F2 1.2581(2) 1.19398(18) 0.48033(4) 0.0824(3) Uani d . 1 . .
F F3 0.8111(2) 1.44958(15) 0.42966(5) 0.0834(3) Uani d . 1 . .
O O1 0.1646(2) 1.24750(13) 0.19113(5) 0.0552(3) Uani d . 1 . .
N N1 0.5532(2) 1.00798(15) 0.25981(4) 0.0386(2) Uani d . 1 . .
N N2 0.4249(2) 0.91747(15) 0.21550(4) 0.0377(2) Uani d . 1 . .
N N3 -0.1882(3) 0.7926(2) 0.04246(6) 0.0592(3) Uani d . 1 . .
C C1 1.1071(3) 0.8366(2) 0.36730(6) 0.0431(3) Uani d . 1 . .
C C2 1.2389(3) 0.9080(3) 0.41488(6) 0.0532(3) Uani d . 1 . .
C C3 1.1375(3) 1.1151(3) 0.43436(6) 0.0533(3) Uani d . 1 . .
C C4 0.9082(3) 1.2479(2) 0.40781(6) 0.0520(3) Uani d . 1 . .
C C5 0.7792(3) 1.1753(2) 0.36057(6) 0.0465(3) Uani d . 1 . .
C C6 0.8779(2) 0.96531(19) 0.33900(5) 0.0381(3) Uani d . 1 . .
C C7 0.7429(2) 0.87952(19) 0.28944(5) 0.0391(3) Uani d . 1 . .
C C8 0.2279(2) 1.05161(17) 0.18276(5) 0.0381(3) Uani d . 1 . .
C C9 0.0888(2) 0.95209(18) 0.13457(5) 0.0381(3) Uani d . 1 . .
C C10 -0.1271(3) 1.0858(2) 0.10359(6) 0.0469(3) Uani d . 1 . .
C C11 -0.2587(3) 0.9994(3) 0.05883(6) 0.0549(3) Uani d . 1 . .
C C12 0.0208(4) 0.6670(3) 0.07203(7) 0.0645(4) Uani d . 1 . .
C C13 0.1642(3) 0.7368(2) 0.11825(7) 0.0555(4) Uani d . 1 . .
O O1W 0.6042(3) 0.46898(15) 0.22162(5) 0.0567(3) Uani d . 1 . .
H H2A 1.388(4) 0.807(3) 0.4315(9) 0.079(5) Uiso d . 1 . .
H H5A 0.619(4) 1.275(3) 0.3436(8) 0.069(5) Uiso d . 1 . .
H H7A 0.798(3) 0.727(2) 0.2805(7) 0.054(4) Uiso d . 1 . .
H H10A -0.178(3) 1.237(3) 0.1110(7) 0.061(4) Uiso d . 1 . .
H H11A -0.398(4) 1.092(3) 0.0388(8) 0.069(5) Uiso d . 1 . .
H H12A 0.087(4) 0.519(3) 0.0585(9) 0.084(6) Uiso d . 1 . .
H H13A 0.316(4) 0.636(3) 0.1371(8) 0.073(5) Uiso d . 1 . .
H H1N2 0.479(3) 0.776(3) 0.2116(8) 0.067(5) Uiso d . 1 . .
H H1W1 0.759(4) 0.402(3) 0.2127(8) 0.071(6) Uiso d . 1 . .
H H2W1 0.499(4) 0.384(4) 0.2232(10) 0.099(7) Uiso 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 N2 . . 116.55(9) ?
C8 N2 N1 . . 117.36(9) ?
C8 N2 H1N2 . . 126.2(11) ?
N1 N2 H1N2 . . 116.5(11) ?
C12 N3 C11 . . 116.24(11) ?
F1 C1 C2 . . 118.25(11) ?
F1 C1 C6 . . 118.70(10) ?
C2 C1 C6 . . 123.04(12) ?
C3 C2 C1 . . 117.80(12) ?
C3 C2 H2A . . 126.1(11) ?
C1 C2 H2A . . 116.1(11) ?
F2 C3 C2 . . 120.48(12) ?
F2 C3 C4 . . 118.53(13) ?
C2 C3 C4 . . 120.99(11) ?
F3 C4 C5 . . 120.41(12) ?
F3 C4 C3 . . 118.89(11) ?
C5 C4 C3 . . 120.70(12) ?
C4 C5 C6 . . 120.06(12) ?
C4 C5 H5A . . 117.3(10) ?
C6 C5 H5A . . 122.7(10) ?
C1 C6 C5 . . 117.41(10) ?
C1 C6 C7 . . 120.67(11) ?
C5 C6 C7 . . 121.89(10) ?
N1 C7 C6 . . 118.93(10) ?
N1 C7 H7A . . 121.8(9) ?
C6 C7 H7A . . 119.2(9) ?
O1 C8 N2 . . 122.04(9) ?
O1 C8 C9 . . 120.84(10) ?
N2 C8 C9 . . 117.12(9) ?
C13 C9 C10 . . 117.67(10) ?
C13 C9 C8 . . 124.60(10) ?
C10 C9 C8 . . 117.72(10) ?
C11 C10 C9 . . 119.15(12) ?
C11 C10 H10A . . 119.8(9) ?
C9 C10 H10A . . 121.0(9) ?
N3 C11 C10 . . 123.93(13) ?
N3 C11 H11A . . 119.1(11) ?
C10 C11 H11A . . 116.9(11) ?
N3 C12 C13 . . 124.42(14) ?
N3 C12 H12A . . 117.9(11) ?
C13 C12 H12A . . 117.5(11) ?
C9 C13 C12 . . 118.58(13) ?
C9 C13 H13A . . 121.8(10) ?
C12 C13 H13A . . 119.6(10) ?
H1W1 O1W H2W1 . . 108.0(19) ?
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
F1 C1 . 1.3454(15) ?
F2 C3 . 1.3445(13) ?
F3 C4 . 1.3463(16) ?
O1 C8 . 1.2299(13) ?
N1 C7 . 1.2737(15) ?
N1 N2 . 1.3791(11) ?
N2 C8 . 1.3477(14) ?
N2 H1N2 . 0.881(18) ?
N3 C12 . 1.326(2) ?
N3 C11 . 1.3324(19) ?
C1 C2 . 1.3800(17) ?
C1 C6 . 1.3877(16) ?
C2 C3 . 1.363(2) ?
C2 H2A . 0.93(2) ?
C3 C4 . 1.381(2) ?
C4 C5 . 1.3699(16) ?
C5 C6 . 1.3922(17) ?
C5 H5A . 0.969(18) ?
C6 C7 . 1.4660(14) ?
C7 H7A . 0.965(15) ?
C8 C9 . 1.5025(14) ?
C9 C13 . 1.3835(17) ?
C9 C10 . 1.3843(17) ?
C10 C11 . 1.3821(17) ?
C10 H10A . 0.953(16) ?
C11 H11A . 0.911(19) ?
C12 C13 . 1.3882(17) ?
C12 H12A . 0.966(19) ?
C13 H13A . 0.963(18) ?
O1W H1W1 . 0.79(2) ?
O1W H2W1 . 0.83(2) ?
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
N2 H1N2 O1W . 0.883(19) 1.921(19) 2.7910(13) 168.1(16) yes
O1W H1W1 O1 1_645 0.79(2) 2.03(2) 2.8263(17) 176.3(18) yes
O1W H2W1 O1 1_545 0.84(2) 2.19(2) 2.9670(17) 155(2) yes
O1W H2W1 N1 1_545 0.84(2) 2.47(2) 3.1024(14) 133.7(19) yes
C7 H7A O1W . 0.967(13) 2.492(14) 3.2576(16) 135.9(12) yes
C13 H13A O1W . 0.963(19) 2.427(18) 3.3308(19) 156.2(14) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 N2 C8 . . . . -178.64(11) ?
F1 C1 C2 C3 . . . . 178.60(12) ?
C6 C1 C2 C3 . . . . -0.2(2) ?
C1 C2 C3 F2 . . . . -179.70(12) ?
C1 C2 C3 C4 . . . . 0.8(2) ?
F2 C3 C4 F3 . . . . -1.2(2) ?
C2 C3 C4 F3 . . . . 178.33(14) ?
F2 C3 C4 C5 . . . . 179.61(13) ?
C2 C3 C4 C5 . . . . -0.8(2) ?
F3 C4 C5 C6 . . . . -178.86(13) ?
C3 C4 C5 C6 . . . . 0.3(2) ?
F1 C1 C6 C5 . . . . -179.11(12) ?
C2 C1 C6 C5 . . . . -0.3(2) ?
F1 C1 C6 C7 . . . . 2.38(18) ?
C2 C1 C6 C7 . . . . -178.84(12) ?
C4 C5 C6 C1 . . . . 0.3(2) ?
C4 C5 C6 C7 . . . . 178.75(12) ?
N2 N1 C7 C6 . . . . -177.37(10) ?
C1 C6 C7 N1 . . . . -172.44(12) ?
C5 C6 C7 N1 . . . . 9.12(19) ?
N1 N2 C8 O1 . . . . 0.66(18) ?
N1 N2 C8 C9 . . . . -179.99(9) ?
O1 C8 C9 C13 . . . . 174.03(13) ?
N2 C8 C9 C13 . . . . -5.32(19) ?
O1 C8 C9 C10 . . . . -4.90(18) ?
N2 C8 C9 C10 . . . . 175.74(11) ?
C13 C9 C10 C11 . . . . 0.8(2) ?
C8 C9 C10 C11 . . . . 179.78(12) ?
C12 N3 C11 C10 . . . . 0.3(2) ?
C9 C10 C11 N3 . . . . -1.0(2) ?
C11 N3 C12 C13 . . . . 0.7(3) ?
C10 C9 C13 C12 . . . . 0.1(2) ?
C8 C9 C13 C12 . . . . -178.85(13) ?
N3 C12 C13 C9 . . . . -0.9(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656035
