#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/58/2205855.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_2205855
loop_
_publ_author_name
'Ma, Jian'
'Zhang, Shu-Ping'
'Sheng, Liang-Quan'
'Fan, Min'
'Yang, Ya-Li'
'Shao, Si-Chang'
_publ_section_title
;
 3,4-Dichlorobenzaldehyde (2-hydroxybenzoyl)hydrazone
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1747
_journal_page_last               o1748
_journal_paper_doi               10.1107/S1600536805014789
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C14 H10 Cl2 N2 O2'
_chemical_formula_moiety         'C14 H10 Cl2 N2 O2'
_chemical_formula_sum            'C14 H10 Cl2 N2 O2'
_chemical_formula_weight         309.14
_chemical_name_systematic
;
3,4-Dichlorobenzaldehyde (2-hydroxybenzoyl)hydrazone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 91.034(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0466(18)
_cell_length_b                   19.314(6)
_cell_length_c                   11.452(3)
_cell_measurement_reflns_used    2023
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.18
_cell_measurement_theta_min      2.76
_cell_volume                     1337.2(7)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2002)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX area-detector'
_diffrn_measurement_method       'φ and 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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6948
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.487
_exptl_absorpt_correction_T_max  0.9047
_exptl_absorpt_correction_T_min  0.8180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0393
_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)+(0.0388P)²+0.6353P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                1580
_reflns_number_total             2363
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bd6005.cif
_cod_data_source_block           I
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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      'P 21/n'
_cod_database_code               2205855
_cod_database_fobs_code          2205855
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Cl1 0.22137(14) 0.98427(5) 0.08566(7) 0.0711(3) Uani d 1 Cl
Cl2 0.10405(12) 1.01197(4) 0.34796(7) 0.0633(3) Uani d 1 Cl
O1 1.2399(3) 0.71663(10) 0.43600(15) 0.0511(5) Uani d 1 O
O2 1.4320(3) 0.73774(11) 0.08884(17) 0.0512(5) Uani d 1 O
H2 1.493(5) 0.7465(17) 0.031(3) 0.078(12) Uiso d 1 H
N1 1.1715(3) 0.76936(12) 0.2636(2) 0.0413(6) Uani d 1 N
H1 1.198(4) 0.7738(12) 0.197(2) 0.034(7) Uiso d 1 H
N2 0.9930(3) 0.80481(11) 0.30581(18) 0.0404(5) Uani d 1 N
C1 1.2895(4) 0.72702(13) 0.3333(2) 0.0384(6) Uani d 1 C
C2 1.4858(4) 0.69291(12) 0.2819(2) 0.0353(6) Uani d 1 C
C3 1.5540(4) 0.69969(13) 0.1665(2) 0.0388(6) Uani d 1 C
C4 1.7469(5) 0.66753(15) 0.1314(3) 0.0480(7) Uani d 1 C
H4 1.786(4) 0.6738(14) 0.058(3) 0.059(9) Uiso d 1 H
C5 1.8695(5) 0.62897(16) 0.2081(3) 0.0537(8) Uani d 1 C
H5 1.999(5) 0.6092(15) 0.185(2) 0.065(9) Uiso d 1 H
C6 1.8047(5) 0.62081(16) 0.3214(3) 0.0533(8) Uani d 1 C
H6 1.890(4) 0.5926(13) 0.372(2) 0.052(8) Uiso d 1 H
C7 1.6152(5) 0.65276(15) 0.3566(2) 0.0472(7) Uani d 1 C
H7 1.571(4) 0.6484(13) 0.436(2) 0.047(7) Uiso d 1 H
C8 0.8762(4) 0.83556(14) 0.2283(3) 0.0430(7) Uani d 1 C
H8 0.906(4) 0.8327(13) 0.149(2) 0.043(7) Uiso d 1 H
C9 0.6857(4) 0.87738(13) 0.2595(2) 0.0391(6) Uani d 1 C
C10 0.5571(4) 0.90682(15) 0.1715(2) 0.0452(7) Uani d 1 C
H10 0.591(4) 0.8982(13) 0.094(3) 0.056(8) Uiso d 1 H
C11 0.3775(4) 0.94783(14) 0.1977(2) 0.0443(7) Uani d 1 C
C12 0.3237(4) 0.95973(13) 0.3122(2) 0.0432(7) Uani d 1 C
C13 0.4513(5) 0.93022(14) 0.4008(3) 0.0478(7) Uani d 1 C
H13 0.404(4) 0.9428(14) 0.477(3) 0.061(8) Uiso d 1 H
C14 0.6287(5) 0.88939(15) 0.3750(2) 0.0459(7) Uani d 1 C
H14 0.716(4) 0.8675(13) 0.433(2) 0.042(7) Uiso d 1 H
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'
Cl Cl 0.1484 0.1585 '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
C3 O2 H2 114(2)
C1 N1 N2 120.6(2)
C1 N1 H1 121.9(18)
N2 N1 H1 117.5(18)
C8 N2 N1 114.7(2)
O1 C1 N1 122.0(2)
O1 C1 C2 120.9(2)
N1 C1 C2 117.1(2)
C7 C2 C3 117.6(2)
C7 C2 C1 116.7(2)
C3 C2 C1 125.7(2)
O2 C3 C4 120.1(2)
O2 C3 C2 120.2(2)
C4 C3 C2 119.7(3)
C5 C4 C3 120.6(3)
C5 C4 H4 122.3(18)
C3 C4 H4 117.1(18)
C4 C5 C6 120.8(3)
C4 C5 H5 119.8(18)
C6 C5 H5 119.3(19)
C7 C6 C5 118.8(3)
C7 C6 H6 121.8(16)
C5 C6 H6 119.3(16)
C6 C7 C2 122.4(3)
C6 C7 H7 119.3(15)
C2 C7 H7 118.2(15)
N2 C8 C9 121.3(2)
N2 C8 H8 122.7(15)
C9 C8 H8 116.0(15)
C10 C9 C14 118.6(2)
C10 C9 C8 119.0(2)
C14 C9 C8 122.4(2)
C11 C10 C9 120.7(3)
C11 C10 H10 119.9(17)
C9 C10 H10 119.4(17)
C12 C11 C10 120.2(3)
C12 C11 Cl1 120.2(2)
C10 C11 Cl1 119.6(2)
C11 C12 C13 119.4(2)
C11 C12 Cl2 121.4(2)
C13 C12 Cl2 119.2(2)
C14 C13 C12 120.5(3)
C14 C13 H13 126.4(17)
C12 C13 H13 113.1(17)
C13 C14 C9 120.6(3)
C13 C14 H14 122.3(15)
C9 C14 H14 117.0(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C11 1.729(3) yes
Cl2 C12 1.723(3) yes
O1 C1 1.236(3) yes
O2 C3 1.360(3) yes
O2 H2 0.79(3) ?
N1 C1 1.339(3) yes
N1 N2 1.373(3) yes
N1 H1 0.79(2) ?
N2 C8 1.272(3) yes
C1 C2 1.488(3) ?
C2 C7 1.386(4) ?
C2 C3 1.398(3) ?
C3 C4 1.387(4) ?
C4 C5 1.361(4) ?
C4 H4 0.89(3) ?
C5 C6 1.371(4) ?
C5 H5 0.92(3) ?
C6 C7 1.369(4) ?
C6 H6 0.94(3) ?
C7 H7 0.95(3) ?
C8 C9 1.457(4) ?
C8 H8 0.94(2) ?
C9 C10 1.384(4) ?
C9 C14 1.392(3) ?
C10 C11 1.381(4) ?
C10 H10 0.93(3) ?
C11 C12 1.377(4) ?
C12 C13 1.386(4) ?
C13 C14 1.368(4) ?
C13 H13 0.95(3) ?
C14 H14 0.94(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
O2 H2 O1 4_675 0.79(3) 1.99(3) 2.724(3) 155(3)
N1 H1 O2 . 0.79(2) 2.02(2) 2.641(3) 135(2)
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
C1 N1 N2 C8 -170.6(2) ?
N2 N1 C1 O1 2.1(4) ?
N2 N1 C1 C2 -177.5(2) ?
O1 C1 C2 C7 -3.7(4) yes
N1 C1 C2 C7 175.9(2) yes
O1 C1 C2 C3 178.5(2) ?
N1 C1 C2 C3 -2.0(4) ?
C7 C2 C3 O2 179.1(2) yes
C1 C2 C3 O2 -3.0(4) yes
C7 C2 C3 C4 -0.9(4) ?
C1 C2 C3 C4 176.9(2) ?
O2 C3 C4 C5 -179.6(3) ?
C2 C3 C4 C5 0.5(4) ?
C3 C4 C5 C6 0.3(5) ?
C4 C5 C6 C7 -0.7(5) ?
C5 C6 C7 C2 0.2(5) ?
C3 C2 C7 C6 0.6(4) ?
C1 C2 C7 C6 -177.5(3) ?
N1 N2 C8 C9 -177.8(2) ?
N2 C8 C9 C10 -176.7(3) ?
N2 C8 C9 C14 3.9(4) ?
C14 C9 C10 C11 0.7(4) ?
C8 C9 C10 C11 -178.8(2) ?
C9 C10 C11 C12 -0.2(4) ?
C9 C10 C11 Cl1 179.6(2) ?
C10 C11 C12 C13 0.0(4) ?
Cl1 C11 C12 C13 -179.8(2) ?
C10 C11 C12 Cl2 178.7(2) ?
Cl1 C11 C12 Cl2 -1.1(3) ?
C11 C12 C13 C14 -0.3(4) ?
Cl2 C12 C13 C14 -179.0(2) ?
C12 C13 C14 C9 0.7(4) ?
C10 C9 C14 C13 -0.9(4) ?
C8 C9 C14 C13 178.6(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5286946
