#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/92/2209225.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_2209225
loop_
_publ_author_name
'Bai, Zheng-Chen'
'Li, Hao'
'Liu, Yu'
'Jing, Zuo-Liang'
_publ_section_title
;
 N'-(2,4-Dichlorobenzylidene)-2-methoxybenzohydrazide
;
_journal_coeditor_code           IS2034
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2295
_journal_page_last               o2296
_journal_paper_doi               10.1107/S1600536806017053
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H12 Cl2 N2 O2'
_chemical_formula_moiety         'C15 H12 Cl2 N2 O2'
_chemical_formula_sum            'C15 H12 Cl2 N2 O2'
_chemical_formula_weight         323.17
_chemical_name_systematic
;
N'-(2,4-Dichlorobenzylidene)-2-methoxybenzohydrazide
;
_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                80.877(5)
_cell_angle_beta                 79.738(5)
_cell_angle_gamma                70.002(5)
_cell_formula_units_Z            2
_cell_length_a                   7.389(3)
_cell_length_b                   7.908(3)
_cell_length_c                   13.575(5)
_cell_measurement_reflns_used    1464
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     729.4(5)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART CCD 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  0.0124
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4004
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.76
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.450
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.247
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2545
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0335
_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)+(0.0509P)²+0.0881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0925
_reflns_number_gt                1968
_reflns_number_total             2545
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2034.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_original_cell_volume        729.3(5)
_cod_database_code               2209225
_cod_database_fobs_code          2209225
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
Cl Cl1 0.06648(8) 0.71971(6) 0.70450(4) 0.06182(19) Uani d . 1
Cl Cl2 0.19051(10) 0.12087(8) 0.53297(4) 0.0722(2) Uani d . 1
O O1 0.4453(3) 0.22317(19) 1.13903(11) 0.0773(5) Uani d . 1
O O2 0.2297(2) 0.77975(16) 1.10523(9) 0.0532(4) Uani d . 1
N N1 0.2780(2) 0.37010(19) 0.96883(10) 0.0421(4) Uani d . 1
N N2 0.2737(2) 0.4664(2) 1.04525(10) 0.0437(4) Uani d . 1
H H2A 0.2156 0.5814 1.0404 0.052 Uiso calc R 1
C C1 0.1407(2) 0.4845(2) 0.71523(13) 0.0386(4) Uani d . 1
C C2 0.1356(3) 0.4060(2) 0.63222(13) 0.0433(4) Uani d . 1
H H2 0.0920 0.4772 0.5743 0.052 Uiso calc R 1
C C3 0.1962(3) 0.2207(3) 0.63711(13) 0.0447(4) Uani d . 1
C C4 0.2617(3) 0.1132(2) 0.72247(14) 0.0474(5) Uani d . 1
H H4 0.3023 -0.0122 0.7248 0.057 Uiso calc R 1
C C5 0.2660(3) 0.1943(2) 0.80389(13) 0.0431(4) Uani d . 1
H H5 0.3107 0.1218 0.8613 0.052 Uiso calc R 1
C C6 0.2056(2) 0.3821(2) 0.80321(12) 0.0372(4) Uani d . 1
C C7 0.2119(3) 0.4655(2) 0.89033(13) 0.0418(4) Uani d . 1
H H7 0.1668 0.5910 0.8886 0.050 Uiso calc R 1
C C8 0.3594(3) 0.3837(2) 1.12844(13) 0.0426(4) Uani d . 1
C C9 0.3384(2) 0.5039(2) 1.20808(13) 0.0386(4) Uani d . 1
C C10 0.2810(3) 0.6932(2) 1.19659(13) 0.0413(4) Uani d . 1
C C11 0.2770(3) 0.7863(3) 1.27585(15) 0.0539(5) Uani d . 1
H H11 0.2407 0.9119 1.2675 0.065 Uiso calc R 1
C C12 0.3268(3) 0.6923(3) 1.36727(16) 0.0594(6) Uani d . 1
H H12 0.3237 0.7551 1.4203 0.071 Uiso calc R 1
C C13 0.3806(3) 0.5073(3) 1.38034(14) 0.0552(5) Uani d . 1
H H13 0.4126 0.4446 1.4422 0.066 Uiso calc R 1
C C14 0.3871(3) 0.4144(3) 1.30131(13) 0.0467(5) Uani d . 1
H H14 0.4250 0.2886 1.3105 0.056 Uiso calc R 1
C C15 0.2049(4) 0.9671(3) 1.08249(19) 0.0776(7) Uani d . 1
H H15A 0.0907 1.0353 1.1229 0.116 Uiso calc R 1
H H15B 0.1908 1.0022 1.0125 0.116 Uiso calc R 1
H H15C 0.3164 0.9905 1.0966 0.116 Uiso calc R 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'
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
C10 O2 C15 119.91(15) ?
C7 N1 N2 115.05(15) yes
C8 N2 N1 121.24(15) yes
C8 N2 H2A 119.4 ?
N1 N2 H2A 119.4 ?
C2 C1 C6 122.30(16) ?
C2 C1 Cl1 116.81(13) ?
C6 C1 Cl1 120.88(13) ?
C3 C2 C1 118.56(16) ?
C3 C2 H2 120.7 ?
C1 C2 H2 120.7 ?
C2 C3 C4 121.38(16) ?
C2 C3 Cl2 118.85(14) ?
C4 C3 Cl2 119.76(14) ?
C5 C4 C3 119.00(17) ?
C5 C4 H4 120.5 ?
C3 C4 H4 120.5 ?
C4 C5 C6 122.06(16) ?
C4 C5 H5 119.0 ?
C6 C5 H5 119.0 ?
C1 C6 C5 116.69(15) ?
C1 C6 C7 122.09(15) yes
C5 C6 C7 121.22(15) yes
N1 C7 C6 121.32(16) yes
N1 C7 H7 119.3 ?
C6 C7 H7 119.3 ?
O1 C8 N2 122.45(16) yes
O1 C8 C9 121.68(16) yes
N2 C8 C9 115.87(15) yes
C14 C9 C10 117.87(16) ?
C14 C9 C8 115.40(16) yes
C10 C9 C8 126.71(15) yes
O2 C10 C11 122.37(17) ?
O2 C10 C9 117.29(14) ?
C11 C10 C9 120.34(17) ?
C12 C11 C10 120.02(19) ?
C12 C11 H11 120.0 ?
C10 C11 H11 120.0 ?
C13 C12 C11 120.46(18) ?
C13 C12 H12 119.8 ?
C11 C12 H12 119.8 ?
C12 C13 C14 119.63(19) ?
C12 C13 H13 120.2 ?
C14 C13 H13 120.2 ?
C13 C14 C9 121.67(18) ?
C13 C14 H14 119.2 ?
C9 C14 H14 119.2 ?
O2 C15 H15A 109.5 ?
O2 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
O2 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 1.7398(18) ?
Cl2 C3 1.7380(18) ?
O1 C8 1.208(2) yes
O2 C10 1.368(2) ?
O2 C15 1.419(2) ?
N1 C7 1.274(2) yes
N1 N2 1.3708(19) yes
N2 C8 1.357(2) yes
N2 H2A 0.8600 ?
C1 C2 1.382(2) ?
C1 C6 1.394(2) yes
C2 C3 1.372(2) ?
C2 H2 0.9300 ?
C3 C4 1.380(3) ?
C4 C5 1.373(2) ?
C4 H4 0.9300 ?
C5 C6 1.396(2) yes
C5 H5 0.9300 ?
C6 C7 1.458(2) yes
C7 H7 0.9300 ?
C8 C9 1.504(2) yes
C9 C14 1.391(2) yes
C9 C10 1.400(2) yes
C10 C11 1.387(2) ?
C11 C12 1.382(3) ?
C11 H11 0.9300 ?
C12 C13 1.369(3) ?
C12 H12 0.9300 ?
C13 C14 1.379(3) ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
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
N2 H2A O2 . 0.86 1.96 2.627(2) 134
C15 H15C O1 1_565 0.96 2.52 3.359(3) 146
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
C7 N1 N2 C8 -172.42(16)
C6 C1 C2 C3 0.2(3)
Cl1 C1 C2 C3 178.91(14)
C1 C2 C3 C4 -0.2(3)
C1 C2 C3 Cl2 -179.91(14)
C2 C3 C4 C5 0.0(3)
Cl2 C3 C4 C5 179.70(14)
C3 C4 C5 C6 0.2(3)
C2 C1 C6 C5 0.0(3)
Cl1 C1 C6 C5 -178.65(13)
C2 C1 C6 C7 179.58(17)
Cl1 C1 C6 C7 0.9(2)
C4 C5 C6 C1 -0.2(3)
C4 C5 C6 C7 -179.80(17)
N2 N1 C7 C6 -179.45(15)
C1 C6 C7 N1 -177.46(17)
C5 C6 C7 N1 2.1(3)
N1 N2 C8 O1 1.0(3)
N1 N2 C8 C9 -178.07(15)
O1 C8 C9 C14 -12.9(3)
N2 C8 C9 C14 166.12(16)
O1 C8 C9 C10 165.13(19)
N2 C8 C9 C10 -15.8(3)
C15 O2 C10 C11 11.8(3)
C15 O2 C10 C9 -168.44(18)
C14 C9 C10 O2 -178.69(16)
C8 C9 C10 O2 3.3(3)
C14 C9 C10 C11 1.1(3)
C8 C9 C10 C11 -176.92(18)
O2 C10 C11 C12 178.78(18)
C9 C10 C11 C12 -1.0(3)
C10 C11 C12 C13 0.1(3)
C11 C12 C13 C14 0.7(3)
C12 C13 C14 C9 -0.6(3)
C10 C9 C14 C13 -0.3(3)
C8 C9 C14 C13 177.94(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654964
2 PubChem 9554841
