#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/13/2221330.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_2221330
loop_
_publ_author_name
'Wu, Hong-Yuan'
_publ_section_title
;
 4-Chloro-N'-(2-methoxybenzylidene)benzohydrazide
;
_journal_coeditor_code           DN2433
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o852
_journal_paper_doi               10.1107/S1600536809010186
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H13 Cl N2 O2'
_chemical_formula_moiety         'C15 H13 Cl N2 O2'
_chemical_formula_sum            'C15 H13 Cl N2 O2'
_chemical_formula_weight         288.72
_chemical_name_systematic
;
4-Chloro-N'-(2-methoxybenzylidene)benzohydrazide
;
_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                93.298(2)
_cell_angle_beta                 100.945(3)
_cell_angle_gamma                106.055(2)
_cell_formula_units_Z            4
_cell_length_a                   7.802(2)
_cell_length_b                   13.395(3)
_cell_length_c                   14.599(2)
_cell_measurement_reflns_used    1723
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.5
_cell_volume                     1429.7(5)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia,
1997) and
PLATON (Spek, 2009)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       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  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0429
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8597
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.43
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'cut from needle'
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.372
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         6134
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0539
_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)+(0.0595P)²+0.2838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1525
_reflns_number_gt                3465
_reflns_number_total             6134
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2433.cif
_cod_data_source_block           I
_cod_database_code               2221330
_cod_database_fobs_code          2221330
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
Cl Cl1 -0.36428(18) 0.35966(9) 0.40462(10) 0.1543(6) Uani d . 1 . .
Cl Cl2 0.01821(14) 0.31778(8) 0.07426(8) 0.1277(4) Uani d . 1 . .
N N1 0.1823(3) 0.75724(14) 0.25213(13) 0.0483(5) Uani d . 1 . .
H H1 0.0681 0.7446 0.2274 0.058 Uiso calc R 1 . .
N N2 0.3077(3) 0.84442(15) 0.23333(14) 0.0507(5) Uani d . 1 . .
N N3 0.6661(2) 0.76354(14) 0.22293(14) 0.0500(5) Uani d . 1 . .
H H3 0.5645 0.7571 0.2402 0.060 Uiso calc R 1 . .
N N4 0.8123(2) 0.85210(14) 0.25581(13) 0.0475(5) Uani d . 1 . .
O O1 0.3995(2) 0.69948(13) 0.33805(12) 0.0609(5) Uani d . 1 . .
O O2 0.1670(4) 0.9429(2) -0.00901(17) 0.0918(7) Uani d . 1 . .
O O3 0.8240(2) 0.69020(14) 0.13798(12) 0.0633(5) Uani d . 1 . .
O O4 0.7265(3) 1.05068(14) 0.44551(13) 0.0713(5) Uani d . 1 . .
C C1 -0.1898(5) 0.4568(3) 0.3777(2) 0.0879(10) Uani d . 1 . .
C C2 -0.0336(6) 0.4345(2) 0.3656(3) 0.0975(11) Uani d . 1 . .
H H2 -0.0226 0.3678 0.3719 0.117 Uiso calc R 1 . .
C C3 0.1072(4) 0.5114(2) 0.3440(2) 0.0776(8) Uani d . 1 . .
H H3A 0.2144 0.4971 0.3372 0.093 Uiso calc R 1 . .
C C4 0.0877(3) 0.60967(18) 0.33272(17) 0.0528(6) Uani d . 1 . .
C C5 -0.0703(3) 0.6296(2) 0.34588(17) 0.0581(6) Uani d . 1 . .
H H5 -0.0835 0.6958 0.3389 0.070 Uiso calc R 1 . .
C C6 -0.2094(4) 0.5536(2) 0.3691(2) 0.0732(8) Uani d . 1 . .
H H6 -0.3147 0.5683 0.3787 0.088 Uiso calc R 1 . .
C C7 0.2386(3) 0.69232(18) 0.30901(17) 0.0493(6) Uani d . 1 . .
C C8 0.2455(3) 0.88706(18) 0.16387(18) 0.0525(6) Uani d . 1 . .
H H8 0.1296 0.8545 0.1273 0.063 Uiso calc R 1 . .
C C9 0.3533(4) 0.9858(2) 0.1410(2) 0.0621(7) Uani d . 1 . .
C C10 0.3066(5) 1.0144(3) 0.0507(3) 0.0809(10) Uani d . 1 . .
C C11 0.4045(7) 1.1090(3) 0.0286(4) 0.1179(17) Uani d . 1 . .
H H11 0.3749 1.1280 -0.0313 0.141 Uiso calc R 1 . .
C C12 0.5443(7) 1.1749(3) 0.0941(5) 0.136(2) Uani d . 1 . .
H H12 0.6091 1.2385 0.0783 0.164 Uiso calc R 1 . .
C C13 0.5913(5) 1.1490(3) 0.1832(4) 0.1147(16) Uani d . 1 . .
H H13 0.6873 1.1945 0.2272 0.138 Uiso calc R 1 . .
C C14 0.4943(4) 1.0544(2) 0.2068(3) 0.0788(9) Uani d . 1 . .
H H14 0.5240 1.0368 0.2673 0.095 Uiso calc R 1 . .
C C15 0.1087(6) 0.9678(4) -0.1012(3) 0.1261(17) Uani d . 1 . .
H H15A 0.0833 1.0339 -0.0971 0.189 Uiso calc R 1 . .
H H15B 0.0002 0.9144 -0.1330 0.189 Uiso calc R 1 . .
H H15C 0.2033 0.9720 -0.1356 0.189 Uiso calc R 1 . .
C C16 0.2096(4) 0.4261(2) 0.0957(2) 0.0792(9) Uani d . 1 . .
C C17 0.1896(4) 0.5239(2) 0.0987(2) 0.0723(8) Uani d . 1 . .
H H17 0.0737 0.5328 0.0875 0.087 Uiso calc R 1 . .
C C18 0.3427(3) 0.6096(2) 0.11840(17) 0.0590(7) Uani d . 1 . .
H H18 0.3294 0.6765 0.1203 0.071 Uiso calc R 1 . .
C C19 0.5153(3) 0.59732(19) 0.13536(17) 0.0528(6) Uani d . 1 . .
C C20 0.5314(4) 0.4971(2) 0.1296(2) 0.0737(8) Uani d . 1 . .
H H20 0.6466 0.4872 0.1391 0.088 Uiso calc R 1 . .
C C21 0.3781(5) 0.4117(2) 0.1100(2) 0.0872(10) Uani d . 1 . .
H H21 0.3898 0.3444 0.1066 0.105 Uiso calc R 1 . .
C C22 0.6829(3) 0.68759(19) 0.16411(17) 0.0507(6) Uani d . 1 . .
C C23 0.7862(3) 0.91383(17) 0.31774(16) 0.0469(5) Uani d . 1 . .
H H23 0.6764 0.8963 0.3378 0.056 Uiso calc R 1 . .
C C24 0.9252(3) 1.01116(17) 0.35755(16) 0.0459(5) Uani d . 1 . .
C C25 0.8937(3) 1.08002(18) 0.42280(17) 0.0522(6) Uani d . 1 . .
C C26 1.0264(4) 1.1724(2) 0.4600(2) 0.0720(8) Uani d . 1 . .
H H26 1.0043 1.2182 0.5036 0.086 Uiso calc R 1 . .
C C27 1.1899(4) 1.1971(2) 0.4332(2) 0.0871(10) Uani d . 1 . .
H H27 1.2791 1.2593 0.4592 0.105 Uiso calc R 1 . .
C C28 1.2236(4) 1.1312(2) 0.3686(2) 0.0836(9) Uani d . 1 . .
H H28 1.3348 1.1485 0.3501 0.100 Uiso calc R 1 . .
C C29 1.0921(3) 1.0396(2) 0.33148(19) 0.0620(7) Uani d . 1 . .
H H29 1.1154 0.9951 0.2873 0.074 Uiso calc R 1 . .
C C30 0.6940(5) 1.1163(2) 0.5169(2) 0.0871(10) Uani d . 1 . .
H H30A 0.7792 1.1197 0.5747 0.131 Uiso calc R 1 . .
H H30B 0.5717 1.0880 0.5256 0.131 Uiso calc R 1 . .
H H30C 0.7093 1.1853 0.4983 0.131 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 N2 . . 119.90(19) ?
C7 N1 H1 . . 120.0 ?
N2 N1 H1 . . 120.0 ?
C8 N2 N1 . . 113.9(2) ?
C22 N3 N4 . . 120.04(19) ?
C22 N3 H3 . . 120.0 ?
N4 N3 H3 . . 120.0 ?
C23 N4 N3 . . 114.35(19) ?
C10 O2 C15 . . 118.5(3) ?
C25 O4 C30 . . 117.5(2) ?
C6 C1 C2 . . 121.2(3) ?
C6 C1 Cl1 . . 119.6(3) ?
C2 C1 Cl1 . . 119.2(3) ?
C1 C2 C3 . . 119.9(3) ?
C1 C2 H2 . . 120.0 ?
C3 C2 H2 . . 120.0 ?
C2 C3 C4 . . 119.6(3) ?
C2 C3 H3A . . 120.2 ?
C4 C3 H3A . . 120.2 ?
C5 C4 C3 . . 119.0(2) ?
C5 C4 C7 . . 121.3(2) ?
C3 C4 C7 . . 119.7(2) ?
C4 C5 C6 . . 121.4(3) ?
C4 C5 H5 . . 119.3 ?
C6 C5 H5 . . 119.3 ?
C1 C6 C5 . . 118.8(3) ?
C1 C6 H6 . . 120.6 ?
C5 C6 H6 . . 120.6 ?
O1 C7 N1 . . 123.1(2) ?
O1 C7 C4 . . 122.8(2) ?
N1 C7 C4 . . 114.1(2) ?
N2 C8 C9 . . 120.9(2) ?
N2 C8 H8 . . 119.5 ?
C9 C8 H8 . . 119.5 ?
C14 C9 C10 . . 119.3(3) ?
C14 C9 C8 . . 121.9(3) ?
C10 C9 C8 . . 118.7(3) ?
O2 C10 C11 . . 125.2(4) ?
O2 C10 C9 . . 115.4(3) ?
C11 C10 C9 . . 119.4(4) ?
C12 C11 C10 . . 120.4(5) ?
C12 C11 H11 . . 119.8 ?
C10 C11 H11 . . 119.8 ?
C11 C12 C13 . . 121.2(4) ?
C11 C12 H12 . . 119.4 ?
C13 C12 H12 . . 119.4 ?
C12 C13 C14 . . 119.3(4) ?
C12 C13 H13 . . 120.3 ?
C14 C13 H13 . . 120.3 ?
C13 C14 C9 . . 120.4(4) ?
C13 C14 H14 . . 119.8 ?
C9 C14 H14 . . 119.8 ?
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 ?
C21 C16 C17 . . 121.0(3) ?
C21 C16 Cl2 . . 119.2(3) ?
C17 C16 Cl2 . . 119.8(3) ?
C16 C17 C18 . . 119.4(3) ?
C16 C17 H17 . . 120.3 ?
C18 C17 H17 . . 120.3 ?
C17 C18 C19 . . 120.8(3) ?
C17 C18 H18 . . 119.6 ?
C19 C18 H18 . . 119.6 ?
C18 C19 C20 . . 118.5(2) ?
C18 C19 C22 . . 122.2(2) ?
C20 C19 C22 . . 119.2(2) ?
C21 C20 C19 . . 120.5(3) ?
C21 C20 H20 . . 119.8 ?
C19 C20 H20 . . 119.8 ?
C16 C21 C20 . . 119.8(3) ?
C16 C21 H21 . . 120.1 ?
C20 C21 H21 . . 120.1 ?
O3 C22 N3 . . 123.7(2) ?
O3 C22 C19 . . 122.4(2) ?
N3 C22 C19 . . 113.9(2) ?
N4 C23 C24 . . 120.9(2) ?
N4 C23 H23 . . 119.5 ?
C24 C23 H23 . . 119.5 ?
C29 C24 C25 . . 117.6(2) ?
C29 C24 C23 . . 121.7(2) ?
C25 C24 C23 . . 120.7(2) ?
O4 C25 C26 . . 123.6(2) ?
O4 C25 C24 . . 116.1(2) ?
C26 C25 C24 . . 120.3(2) ?
C27 C26 C25 . . 120.3(3) ?
C27 C26 H26 . . 119.8 ?
C25 C26 H26 . . 119.8 ?
C26 C27 C28 . . 120.5(3) ?
C26 C27 H27 . . 119.7 ?
C28 C27 H27 . . 119.7 ?
C27 C28 C29 . . 119.3(3) ?
C27 C28 H28 . . 120.4 ?
C29 C28 H28 . . 120.4 ?
C28 C29 C24 . . 122.0(2) ?
C28 C29 H29 . . 119.0 ?
C24 C29 H29 . . 119.0 ?
O4 C30 H30A . . 109.5 ?
O4 C30 H30B . . 109.5 ?
H30A C30 H30B . . 109.5 ?
O4 C30 H30C . . 109.5 ?
H30A C30 H30C . . 109.5 ?
H30B C30 H30C . . 109.5 ?
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
Cl1 C1 . 1.727(3) ?
Cl2 C16 . 1.733(3) ?
N1 C7 . 1.340(3) ?
N1 N2 . 1.379(2) ?
N1 H1 . 0.8600 ?
N2 C8 . 1.274(3) ?
N3 C22 . 1.344(3) ?
N3 N4 . 1.384(2) ?
N3 H3 . 0.8600 ?
N4 C23 . 1.273(3) ?
O1 C7 . 1.222(3) ?
O2 C10 . 1.353(4) ?
O2 C15 . 1.426(4) ?
O3 C22 . 1.224(3) ?
O4 C25 . 1.364(3) ?
O4 C30 . 1.429(3) ?
C1 C6 . 1.356(5) ?
C1 C2 . 1.372(5) ?
C2 C3 . 1.382(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.382(4) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.377(3) ?
C4 C7 . 1.486(3) ?
C5 C6 . 1.377(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C8 C9 . 1.453(3) ?
C8 H8 . 0.9300 ?
C9 C14 . 1.385(4) ?
C9 C10 . 1.402(4) ?
C10 C11 . 1.378(5) ?
C11 C12 . 1.363(7) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.374(7) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.384(5) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 C21 . 1.360(4) ?
C16 C17 . 1.361(4) ?
C17 C18 . 1.379(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.379(3) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.382(4) ?
C19 C22 . 1.485(3) ?
C20 C21 . 1.377(4) ?
C20 H20 . 0.9300 ?
C21 H21 . 0.9300 ?
C23 C24 . 1.451(3) ?
C23 H23 . 0.9300 ?
C24 C29 . 1.384(3) ?
C24 C25 . 1.390(3) ?
C25 C26 . 1.378(3) ?
C26 C27 . 1.364(4) ?
C26 H26 . 0.9300 ?
C27 C28 . 1.365(4) ?
C27 H27 . 0.9300 ?
C28 C29 . 1.367(4) ?
C28 H28 . 0.9300 ?
C29 H29 . 0.9300 ?
C30 H30A . 0.9600 ?
C30 H30B . 0.9600 ?
C30 H30C . 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
N1 H1 O3 1_455 0.86 2.01 2.840(3) 161.9
N3 H3 O1 . 0.86 2.14 2.897(3) 146.9
N3 H3 N2 . 0.86 2.57 3.292(3) 141.6
