#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/30/8103080.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8103080
loop_
_publ_author_name
'Jun Xu'
'You-Qin Shu'
'Ping Hu'
_publ_section_title
;
 Crystal structure of
 N'-(3,5-dichloro-2-hydroxybenzylidene)isonicotinohydrazide, C13H9Cl2N3O2
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              63
_journal_volume                  226
_journal_year                    2011
_chemical_formula_structural     'C13 H9 Cl2 N3 O2'
_chemical_formula_sum            'C13 H9 Cl2 N3 O2'
_chemical_formula_weight         310.13
_chemical_name_systematic
;
N'-(3,5-dichloro-2-hydroxybenzylidene)isonicotinohydrazide
;
_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                 90.8940(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.06070(10)
_cell_length_b                   10.7551(2)
_cell_length_c                   15.6323(2)
_cell_measurement_reflns_used    2625
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.59
_cell_volume                     1355.06(3)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       '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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10988
_diffrn_reflns_theta_full        27.63
_diffrn_reflns_theta_max         27.63
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.483
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Bruker, 1998)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0189(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3131
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0340
_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)+(0.0442P)²+0.3299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0941
_reflns_number_gt                2580
_reflns_number_total             3131
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-3262.cff
_cod_data_source_block           m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      P21/c
_cod_database_code               8103080
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl2 Cl 0.18680(5) 0.54537(4) 0.05031(3) 0.05558(15) Uani 1 1 d .
Cl1 Cl -0.05034(7) 0.86108(5) 0.28548(3) 0.06986(18) Uani 1 1 d .
O1 O -0.19721(17) 0.98759(12) 0.14130(8) 0.0541(3) Uani 1 1 d .
N2 N -0.35002(16) 1.07412(12) -0.08360(8) 0.0417(3) Uani 1 1 d .
H2A H -0.3468 1.0497 -0.1359 0.050 Uiso 1 1 calc R
N1 N -0.27190(15) 1.00966(12) -0.01913(8) 0.0411(3) Uani 1 1 d .
C6 C -0.10186(17) 0.84671(13) 0.03159(9) 0.0370(3) Uani 1 1 d .
C8 C -0.43298(18) 1.17870(14) -0.06074(9) 0.0399(3) Uani 1 1 d .
C7 C -0.18590(18) 0.91457(14) -0.03703(9) 0.0407(3) Uani 1 1 d .
H7A H -0.1766 0.8885 -0.0935 0.049 Uiso 1 1 calc R
C1 C -0.11351(18) 0.88563(14) 0.11759(9) 0.0400(3) Uani 1 1 d .
C9 C -0.50281(17) 1.25665(14) -0.13255(9) 0.0377(3) Uani 1 1 d .
C5 C -0.00830(18) 0.74189(14) 0.01238(9) 0.0398(3) Uani 1 1 d .
H5A H 0.0021 0.7170 -0.0443 0.048 Uiso 1 1 calc R
C3 C 0.05527(19) 0.70866(15) 0.16115(10) 0.0444(4) Uani 1 1 d .
H3A H 0.1049 0.6613 0.2043 0.053 Uiso 1 1 calc R
C4 C 0.06868(18) 0.67501(14) 0.07616(10) 0.0407(3) Uani 1 1 d .
O2 O -0.44641(16) 1.21083(11) 0.01344(7) 0.0543(3) Uani 1 1 d .
C10 C -0.5962(2) 1.35875(16) -0.11090(10) 0.0478(4) Uani 1 1 d .
H10A H -0.6195 1.3748 -0.0539 0.057 Uiso 1 1 calc R
C2 C -0.0335(2) 0.81409(15) 0.18012(9) 0.0433(3) Uani 1 1 d .
N N -0.62434(18) 1.42085(14) -0.25705(9) 0.0527(3) Uani 1 1 d .
C11 C -0.6548(2) 1.43684(17) -0.17407(11) 0.0540(4) Uani 1 1 d .
H11A H -0.7192 1.5045 -0.1581 0.065 Uiso 1 1 calc R
C13 C -0.4728(2) 1.23761(16) -0.21822(10) 0.0508(4) Uani 1 1 d .
H13A H -0.4116 1.1692 -0.2359 0.061 Uiso 1 1 calc R
C12 C -0.5350(2) 1.32174(17) -0.27745(10) 0.0556(4) Uani 1 1 d .
H12A H -0.5130 1.3081 -0.3349 0.067 Uiso 1 1 calc R
H1A H -0.235(3) 1.017(2) 0.0981(16) 0.076(7) Uiso 1 1 d .
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
C1 O1 H1A 105.7(17)
C8 N2 N1 116.63(12)
C8 N2 H2A 121.7
N1 N2 H2A 121.7
C7 N1 N2 119.51(13)
C5 C6 C1 119.32(13)
C5 C6 C7 119.65(13)
C1 C6 C7 121.03(14)
O2 C8 N2 122.49(14)
O2 C8 C9 121.04(14)
N2 C8 C9 116.43(13)
N1 C7 C6 119.41(14)
N1 C7 H7A 120.3
C6 C7 H7A 120.3
O1 C1 C2 119.09(13)
O1 C1 C6 123.08(14)
C2 C1 C6 117.83(14)
C10 C9 C13 117.51(14)
C10 C9 C8 117.45(13)
C13 C9 C8 124.93(14)
C4 C5 C6 120.60(13)
C4 C5 H5A 119.7
C6 C5 H5A 119.7
C2 C3 C4 118.14(14)
C2 C3 H3A 120.9
C4 C3 H3A 120.9
C5 C4 C3 121.36(14)
C5 C4 Cl2 119.68(12)
C3 C4 Cl2 118.96(12)
C11 C10 C9 119.60(15)
C11 C10 H10A 120.2
C9 C10 H10A 120.2
C3 C2 C1 122.70(14)
C3 C2 Cl1 119.66(12)
C1 C2 Cl1 117.64(12)
C12 N C11 116.44(14)
N C11 C10 123.57(16)
N C11 H11A 118.2
C10 C11 H11A 118.2
C9 C13 C12 119.03(16)
C9 C13 H13A 120.5
C12 C13 H13A 120.5
N C12 C13 123.82(16)
N C12 H12A 118.1
C13 C12 H12A 118.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl2 C4 1.7396(16)
Cl1 C2 1.7301(15)
O1 C1 1.3427(19)
O1 H1A 0.80(2)
N2 C8 1.359(2)
N2 N1 1.3685(17)
N2 H2A 0.8600
N1 C7 1.269(2)
C6 C5 1.392(2)
C6 C1 1.4127(19)
C6 C7 1.456(2)
C8 O2 1.2165(18)
C8 C9 1.503(2)
C7 H7A 0.9300
C1 C2 1.394(2)
C9 C10 1.377(2)
C9 C13 1.380(2)
C5 C4 1.370(2)
C5 H5A 0.9300
C3 C2 1.376(2)
C3 C4 1.383(2)
C3 H3A 0.9300
C10 C11 1.375(2)
C10 H10A 0.9300
N C12 1.328(2)
N C11 1.335(2)
C11 H11A 0.9300
C13 C12 1.383(2)
C13 H13A 0.9300
C12 H12A 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A N 0.86 2.18 2.9915(18) 156.8 2_444
O1 H1A N1 0.80(2) 1.85(3) 2.5810(18) 151(2) .
