#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2008084.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_2008084
loop_
_publ_author_name
'Lu, Z.-L.'
'Kang, B.-S.'
'Fun, H.-K.'
'Razak, I. A.'
'Chinnakali, K.'
_publ_section_title
;
 <i>o</i>-Chlorobenzaldehyde nicotinoylhydrazone dihydrate
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              89
_journal_page_last               91
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C13 H10 Cl N3 O , 2H2 O'
_chemical_formula_sum            'C13 H14 Cl N3 O3'
_chemical_formula_weight         295.72
_chemical_name_systematic
;
o-Chlorobenzaldehyde Nicotinoylhydrazone Dihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.506(2)
_cell_angle_beta                 74.124(2)
_cell_angle_gamma                79.242(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7970(6)
_cell_length_b                   9.4921(7)
_cell_length_c                   9.7074(7)
_cell_measurement_reflns_used    2848
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      3.00
_cell_volume                     678.21(9)
_computing_cell_refinement       'SAINT (Siemens, 1996b)'
_computing_data_collection       'SMART (Siemens, 1996a)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL; PARST (Nardelli, 1995)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Siemens, 1996c)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device
;
Siemens SMART CCD area detector diffractometer
;
_diffrn_measurement_method       '\w 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  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5309
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  0.9602
_exptl_absorpt_correction_T_min  0.8771
_exptl_absorpt_correction_type   'empirical using SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.344
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3793
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0710P)^2^+0.1826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_ref         0.1506
_reflns_number_gt                2710
_reflns_number_total             3793
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    ha1232.cif
_[local]_cod_data_source_block   lg001m
_cod_database_code               2008084
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_occupancy
_atom_site_type_symbol
Cl 1.14739(9) -0.41769(6) 0.37853(6) 0.05421(19) Uani d 1 Cl
O1 0.5981(2) 0.25254(17) 0.39387(16) 0.0529(4) Uani d 1 O
O1W 0.7051(3) -0.1704(2) 0.7015(2) 0.0602(5) Uani d 1 O
O2W 1.0190(3) -0.2946(2) 0.7607(2) 0.0554(4) Uani d 1 O
N1 0.2230(3) 0.4187(2) 0.7693(2) 0.0518(5) Uani d 1 N
N2 0.7198(2) 0.05904(18) 0.49690(18) 0.0386(4) Uani d 1 N
N3 0.8478(2) 0.01240(17) 0.36856(17) 0.0376(4) Uani d 1 N
C1 0.2085(3) 0.3420(2) 0.8862(2) 0.0475(5) Uani d 1 C
C2 0.3174(3) 0.2112(2) 0.8900(2) 0.0461(5) Uani d 1 C
C3 0.4475(3) 0.1533(2) 0.7665(2) 0.0418(4) Uani d 1 C
C4 0.4645(2) 0.2299(2) 0.6426(2) 0.0348(4) Uani d 1 C
C5 0.3499(3) 0.3624(2) 0.6506(2) 0.0455(5) Uani d 1 C
C6 0.5990(3) 0.1822(2) 0.5004(2) 0.0368(4) Uani d 1 C
C7 0.9504(3) -0.1087(2) 0.3697(2) 0.0363(4) Uani d 1 C
C8 1.0866(2) -0.17194(19) 0.23774(19) 0.0334(4) Uani d 1 C
C9 1.1229(3) -0.0932(2) 0.1134(2) 0.0399(4) Uani d 1 C
C10 1.2374(3) -0.1567(2) -0.0145(2) 0.0468(5) Uani d 1 C
C11 1.3174(3) -0.3002(2) -0.0218(2) 0.0488(5) Uani d 1 C
C12 1.2891(3) -0.3791(2) 0.0994(2) 0.0450(5) Uani d 1 C
C13 1.1763(3) -0.3143(2) 0.2280(2) 0.0360(4) Uani d 1 C
H1 0.119(4) 0.384(3) 0.964(3) 0.057(7) Uiso d 1 H
H2 0.304(4) 0.166(3) 0.981(3) 0.070(9) Uiso d 1 H
H3 0.524(4) 0.068(3) 0.767(3) 0.066(8) Uiso d 1 H
H5 0.364(4) 0.418(3) 0.570(3) 0.065(8) Uiso d 1 H
H7 0.937(3) -0.159(3) 0.455(3) 0.053(7) Uiso d 1 H
H9 1.071(3) -0.001(2) 0.123(2) 0.035(5) Uiso d 1 H
H10 1.252(4) -0.096(3) -0.100(3) 0.068(8) Uiso d 1 H
H11 1.394(4) -0.350(3) -0.110(3) 0.061(7) Uiso d 1 H
H12 1.334(4) -0.478(3) 0.100(3) 0.057(7) Uiso d 1 H
H1N2 0.717(4) 0.000(3) 0.567(3) 0.057(7) Uiso d 1 H
H1W1 0.792(5) -0.211(4) 0.716(4) 0.082(12) Uiso d 1 H
H2W1 0.641(5) -0.219(4) 0.685(4) 0.091(14) Uiso d 1 H
H1W2 1.069(5) -0.373(4) 0.765(4) 0.076(10) Uiso d 1 H
H2W2 1.100(5) -0.254(4) 0.731(4) 0.086(12) Uiso d 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl 0.0674(4) 0.0434(3) 0.0470(3) -0.0046(2) -0.0122(3) 0.0156(2)
O1 0.0558(9) 0.0529(9) 0.0385(8) 0.0050(7) -0.0044(7) 0.0120(6)
O1W 0.0629(12) 0.0465(9) 0.0685(12) -0.0016(9) -0.0200(10) 0.0132(8)
O2W 0.0520(10) 0.0441(9) 0.0628(11) 0.0004(8) -0.0103(8) 0.0071(8)
N1 0.0493(10) 0.0405(9) 0.0533(11) 0.0068(8) -0.0043(8) -0.0022(8)
N2 0.0389(9) 0.0372(8) 0.0319(8) 0.0016(7) -0.0028(7) 0.0005(6)
N3 0.0373(8) 0.0383(8) 0.0318(8) -0.0025(7) -0.0034(6) -0.0034(6)
C1 0.0424(11) 0.0456(11) 0.0440(11) -0.0028(9) 0.0018(9) -0.0073(9)
C2 0.0507(12) 0.0430(11) 0.0379(10) -0.0061(9) -0.0030(9) 0.0010(8)
C3 0.0447(11) 0.0354(9) 0.0385(10) 0.0003(8) -0.0059(8) 0.0033(8)
C4 0.0335(9) 0.0335(9) 0.0349(9) -0.0039(7) -0.0068(7) -0.0005(7)
C5 0.0440(11) 0.0398(10) 0.0459(11) 0.0016(8) -0.0078(9) 0.0053(8)
C6 0.0371(9) 0.0365(9) 0.0342(9) -0.0047(8) -0.0071(7) 0.0019(7)
C7 0.0392(10) 0.0357(9) 0.0305(9) -0.0036(8) -0.0063(7) -0.0004(7)
C8 0.0349(9) 0.0323(8) 0.0306(9) -0.0039(7) -0.0067(7) -0.0014(7)
C9 0.0441(11) 0.0343(9) 0.0355(10) -0.0004(8) -0.0064(8) 0.0019(7)
C10 0.0506(12) 0.0471(11) 0.0350(10) -0.0010(9) -0.0047(9) 0.0057(8)
C11 0.0508(12) 0.0501(12) 0.0355(10) 0.0042(10) -0.0041(9) -0.0056(9)
C12 0.0477(11) 0.0341(10) 0.0452(11) 0.0051(9) -0.0083(9) -0.0042(8)
C13 0.0391(10) 0.0343(9) 0.0341(9) -0.0065(7) -0.0098(7) 0.0042(7)
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C1 N1 C5 117.00(19) yes
C6 N2 N3 118.34(16) yes
C7 N3 N2 115.45(17) yes
N1 C1 C2 123.5(2) yes
C1 C2 C3 119.1(2) ?
C2 C3 C4 118.73(19) ?
C3 C4 C5 117.72(18) ?
C3 C4 C6 125.26(17) ?
C5 C4 C6 117.02(17) ?
N1 C5 C4 123.9(2) ?
O1 C6 N2 122.44(18) yes
O1 C6 C4 121.11(17) yes
N2 C6 C4 116.45(16) ?
N3 C7 C8 120.27(17) yes
C13 C8 C9 117.32(17) ?
C13 C8 C7 121.58(16) ?
C9 C8 C7 120.98(17) ?
C10 C9 C8 121.07(18) ?
C9 C10 C11 120.0(2) ?
C12 C11 C10 120.24(19) ?
C11 C12 C13 119.52(19) ?
C12 C13 C8 121.71(17) ?
C12 C13 Cl 117.79(15) ?
C8 C13 Cl 120.49(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C13 1.7393(19) yes
O1 C6 1.227(2) yes
N1 C1 1.333(3) yes
N1 C5 1.335(3) yes
N2 C6 1.352(3) yes
N2 N3 1.382(2) yes
N3 C7 1.274(2) yes
C1 C2 1.373(3) ?
C2 C3 1.380(3) ?
C3 C4 1.388(3) ?
C4 C5 1.389(3) ?
C4 C6 1.501(3) ?
C7 C8 1.470(3) ?
C8 C13 1.392(3) ?
C8 C9 1.405(3) ?
C9 C10 1.381(3) ?
C10 C11 1.382(3) ?
C11 C12 1.378(3) ?
C12 C13 1.386(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
_geom_hbond_publ_flag
N2 H1N2 O1W 1_555 0.88(3) 2.07(3) 2.932(3) 168(3) yes
C3 H3 O1W 1_555 0.91(3) 2.42(3) 3.303(3) 163(2) yes
O1W H1W1 O2W 1_555 0.76(4) 1.96(4) 2.719(3) 174(4) yes
O1W H2W1 O1 2_656 0.79(4) 2.27(4) 2.992(3) 152(4) yes
O2W H2W2 O1 2_756 0.79(4) 2.34(4) 3.051(3) 151(4) yes
O2W H2W2 N3 2_756 0.79(4) 2.54(4) 3.177(3) 139(4) yes
O2W H1W2 N1 1_645 0.78(4) 2.12(4) 2.898(3) 176(4) 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
_geom_torsion_publ_flag
C6 N2 N3 C7 -175.73(18) yes
C5 N1 C1 C2 0.8(4) ?
N1 C1 C2 C3 -1.2(4) ?
C1 C2 C3 C4 0.4(3) ?
C2 C3 C4 C5 0.7(3) ?
C2 C3 C4 C6 179.8(2) ?
C1 N1 C5 C4 0.4(4) ?
C3 C4 C5 N1 -1.2(3) ?
C6 C4 C5 N1 179.6(2) ?
N3 N2 C6 O1 0.7(3) yes
N3 N2 C6 C4 -179.00(17) yes
C3 C4 C6 O1 175.7(2) ?
C5 C4 C6 O1 -5.1(3) yes
C3 C4 C6 N2 -4.5(3) yes
C5 C4 C6 N2 174.62(19) ?
N2 N3 C7 C8 177.46(17) yes
N3 C7 C8 C13 -167.62(19) ?
N3 C7 C8 C9 8.3(3) yes
C13 C8 C9 C10 2.6(3) ?
C7 C8 C9 C10 -173.5(2) ?
C8 C9 C10 C11 0.4(3) ?
C9 C10 C11 C12 -2.6(4) ?
C10 C11 C12 C13 1.6(4) ?
C11 C12 C13 C8 1.6(3) ?
C11 C12 C13 Cl -179.15(18) ?
C9 C8 C13 C12 -3.6(3) ?
C7 C8 C13 C12 172.49(19) ?
C9 C8 C13 Cl 177.17(15) ?
C7 C8 C13 Cl -6.8(3) ?