#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/92/2229298.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_2229298
loop_
_publ_author_name
'Huang, Yan-Lan'
'Li, Deng-Feng'
'Sun, Jian'
'Gao, Jin-Hua'
'Shan, Shang'
_publ_section_title
;
 (E)-Benzaldehyde (2,4,6-trichlorophenyl)hydrazone
;
_journal_coeditor_code           XU5149
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o528
_journal_paper_doi               10.1107/S160053681100328X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H9 Cl3 N2'
_chemical_formula_moiety         'C13 H9 Cl3 N2'
_chemical_formula_sum            'C13 H9 Cl3 N2'
_chemical_formula_weight         299.57
_chemical_name_systematic
;
(E)-Benzaldehyde (2,4,6-trichlorophenyl)hydrazone
;
_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                 98.739(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.913(6)
_cell_length_b                   12.867(5)
_cell_length_c                   7.652(3)
_cell_measurement_reflns_used    4171
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.3
_cell_measurement_theta_min      2.8
_cell_volume                     1353.9(9)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_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  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11730
_diffrn_reflns_theta_full        25.19
_diffrn_reflns_theta_max         25.19
_diffrn_reflns_theta_min         2.96
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.320
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2436
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0407
_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)+(0.0449P)²+0.4002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1045
_reflns_number_gt                1936
_reflns_number_total             2436
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5149.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229298
_cod_database_fobs_code          2229298
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_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 0.82868(5) 0.03185(5) 0.52523(10) 0.0786(2) Uani d . 1 . .
Cl Cl2 1.16441(5) 0.21670(7) 0.78646(11) 0.0897(3) Uani d . 1 . .
Cl Cl3 0.85826(6) 0.45120(5) 0.53336(10) 0.0877(3) Uani d . 1 . .
N N1 0.75114(15) 0.24687(17) 0.4714(3) 0.0746(6) Uani d . 1 . .
H H1N 0.7271 0.1962 0.3849 0.089 Uiso d R 1 . .
N N2 0.69094(13) 0.30372(14) 0.5622(2) 0.0566(5) Uani d . 1 . .
C C1 0.84849(16) 0.24097(18) 0.5442(3) 0.0557(6) Uani d . 1 . .
C C2 0.89458(15) 0.14534(18) 0.5762(3) 0.0548(5) Uani d . 1 . .
C C3 0.99117(16) 0.13659(19) 0.6484(3) 0.0595(6) Uani d . 1 . .
H H3 1.0203 0.0717 0.6674 0.071 Uiso calc R 1 . .
C C4 1.04329(16) 0.2259(2) 0.6915(3) 0.0612(6) Uani d . 1 . .
C C5 1.00210(17) 0.3222(2) 0.6597(3) 0.0638(6) Uani d . 1 . .
H H5 1.0386 0.3821 0.6883 0.077 Uiso calc R 1 . .
C C6 0.90617(18) 0.32876(19) 0.5850(3) 0.0603(6) Uani d . 1 . .
C C7 0.59985(17) 0.29350(17) 0.5147(3) 0.0582(6) Uani d . 1 . .
H H7 0.5769 0.2464 0.4258 0.070 Uiso calc R 1 . .
C C8 0.53090(15) 0.35459(18) 0.5976(3) 0.0535(5) Uani d . 1 . .
C C9 0.56026(17) 0.44135(18) 0.6979(3) 0.0561(5) Uani d . 1 . .
H H9 0.6254 0.4608 0.7146 0.067 Uiso calc R 1 . .
C C10 0.4942(2) 0.4996(2) 0.7737(3) 0.0760(7) Uani d . 1 . .
H H10 0.5151 0.5578 0.8411 0.091 Uiso calc R 1 . .
C C11 0.3983(2) 0.4720(3) 0.7501(4) 0.0934(10) Uani d . 1 . .
H H11 0.3539 0.5115 0.8011 0.112 Uiso calc R 1 . .
C C12 0.3676(2) 0.3869(3) 0.6520(5) 0.0952(10) Uani d . 1 . .
H H12 0.3022 0.3683 0.6369 0.114 Uiso calc R 1 . .
C C13 0.43269(18) 0.3272(2) 0.5741(4) 0.0758(7) Uani d . 1 . .
H H13 0.4110 0.2694 0.5066 0.091 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'
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
N2 N1 C1 . . 117.26(18) ?
N2 N1 H1N . . 122.5 ?
C1 N1 H1N . . 117.4 ?
C7 N2 N1 . . 117.19(19) ?
N1 C1 C2 . . 121.0(2) ?
N1 C1 C6 . . 122.7(2) ?
C2 C1 C6 . . 116.3(2) ?
C3 C2 C1 . . 122.5(2) ?
C3 C2 Cl1 . . 118.09(18) ?
C1 C2 Cl1 . . 119.38(18) ?
C4 C3 C2 . . 118.4(2) ?
C4 C3 H3 . . 120.8 ?
C2 C3 H3 . . 120.8 ?
C3 C4 C5 . . 121.5(2) ?
C3 C4 Cl2 . . 119.22(19) ?
C5 C4 Cl2 . . 119.3(2) ?
C4 C5 C6 . . 118.9(2) ?
C4 C5 H5 . . 120.6 ?
C6 C5 H5 . . 120.6 ?
C5 C6 C1 . . 122.3(2) ?
C5 C6 Cl3 . . 117.8(2) ?
C1 C6 Cl3 . . 119.84(18) ?
N2 C7 C8 . . 120.9(2) ?
N2 C7 H7 . . 119.6 ?
C8 C7 H7 . . 119.6 ?
C9 C8 C13 . . 118.5(2) ?
C9 C8 C7 . . 121.3(2) ?
C13 C8 C7 . . 120.3(2) ?
C10 C9 C8 . . 120.9(2) ?
C10 C9 H9 . . 119.6 ?
C8 C9 H9 . . 119.6 ?
C11 C10 C9 . . 120.2(3) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C12 C11 C10 . . 120.1(3) ?
C12 C11 H11 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
C11 C12 C13 . . 120.8(3) ?
C11 C12 H12 . . 119.6 ?
C13 C12 H12 . . 119.6 ?
C12 C13 C8 . . 119.7(3) ?
C12 C13 H13 . . 120.2 ?
C8 C13 H13 . . 120.2 ?
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 C2 . 1.737(2) ?
Cl2 C4 . 1.735(2) ?
Cl3 C6 . 1.733(2) ?
N1 N2 . 1.377(3) ?
N1 C1 . 1.386(3) ?
N1 H1N . 0.9526 ?
N2 C7 . 1.271(3) ?
C1 C2 . 1.392(3) ?
C1 C6 . 1.393(3) ?
C2 C3 . 1.378(3) ?
C3 C4 . 1.372(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.372(3) ?
C5 C6 . 1.372(3) ?
C5 H5 . 0.9300 ?
C7 C8 . 1.458(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.381(3) ?
C8 C13 . 1.396(3) ?
C9 C10 . 1.380(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.367(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.359(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.389(4) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
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
N1 H1N N2 4_565 0.95 2.44 3.183(3) 134 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7837823
