#------------------------------------------------------------------------------
#$Date: 2021-04-10 08:21:54 +0300 (Sat, 10 Apr 2021) $
#$Revision: 264039 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/16/1561634.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_1561634
loop_
_publ_author_name
'El-Hiti, Gamal A'
'Abdel-Wahab, Bakr F.'
'Yousif, Emad'
'Hegazy, Amany S.'
'Kariuki, Benson M.'
_publ_section_title
;
 2-(2,4-Dichlorophenoxy)-N'-[2-(2,4-dichlorophenoxy)acetyl]acetohydrazide
;
_journal_coeditor_code           HB4380
_journal_issue                   4
_journal_name_full               IUCrData
_journal_page_first              x210318
_journal_paper_doi               10.1107/S2414314621003187
_journal_volume                  6
_journal_year                    2021
_chemical_formula_iupac          'C16 H12 Cl4 N2 O4'
_chemical_formula_moiety         'C16 H12 Cl4 N2 O4'
_chemical_formula_sum            'C16 H12 Cl4 N2 O4'
_chemical_formula_weight         438.08
_chemical_name_systematic
;
2-(2,4-Dichlorophenoxy)-N'-[2-(2,4-dichlorophenoxy)acetyl]acetohydrazide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 100.842(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.7398(4)
_cell_length_b                   4.6540(2)
_cell_length_c                   20.1866(9)
_cell_measurement_reflns_used    2218
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.9170
_cell_measurement_theta_min      4.5890
_cell_volume                     898.71(7)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), Mercury (Macrae et al,
2020)
;
_computing_publication_material
;
CHEMDRAW Ultra (Cambridge Soft, 2016)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type
'Rigaku Oxford Diffraction SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5415
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.173
_diffrn_reflns_theta_min         4.460
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.224
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysalisPro; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.009
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.423
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1797
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0525
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0898P)²+0.4345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1526
_reflns_number_gt                1504
_reflns_number_total             1797
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4380sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1561634
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.436
_shelx_estimated_absorpt_t_max   0.946
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.8216(2) 0.7834(5) 0.36947(12) 0.0365(5) Uani d 1 . .
C C2 0.8980(3) 0.5906(6) 0.33765(14) 0.0412(6) Uani d 1 . .
C C3 0.8527(3) 0.5101(7) 0.27100(16) 0.0526(7) Uani d 1 . .
H H3 0.903880 0.379893 0.250485 0.063 Uiso calc 1 . .
C C4 0.7314(3) 0.6258(8) 0.23597(15) 0.0557(7) Uani d 1 . .
C C5 0.6554(3) 0.8206(8) 0.26484(16) 0.0571(8) Uani d 1 . .
H H5 0.574178 0.899439 0.239873 0.069 Uiso calc 1 . .
C C6 0.7006(3) 0.8997(7) 0.33185(15) 0.0479(6) Uani d 1 . .
H H6 0.649162 1.032065 0.351606 0.057 Uiso calc 1 . .
C C7 0.7949(3) 1.0250(5) 0.47047(14) 0.0381(6) Uani d 1 . .
H H7A 0.771884 1.200592 0.444919 0.046 Uiso calc 1 . .
H H7B 0.850851 1.075711 0.513877 0.046 Uiso calc 1 . .
C C8 0.6610(2) 0.8789(5) 0.48107(12) 0.0333(5) Uani d 1 . .
N N1 0.5616(2) 1.0565(4) 0.49304(10) 0.0322(4) Uani d 1 . .
H H1 0.573575 1.239427 0.492170 0.039 Uiso calc 1 . .
O O1 0.87343(17) 0.8420(4) 0.43541(9) 0.0396(4) Uani d 1 . .
O O2 0.6471(2) 0.6192(4) 0.48048(13) 0.0548(6) Uani d 1 . .
Cl Cl1 1.05074(8) 0.44859(19) 0.38265(4) 0.0618(3) Uani d 1 . .
Cl Cl2 0.67176(10) 0.5161(3) 0.15306(4) 0.0858(4) Uani d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
O1 C1 C6 . . 125.4(2) ?
O1 C1 C2 . . 116.6(2) ?
C6 C1 C2 . . 118.0(2) ?
C3 C2 C1 . . 121.4(3) ?
C3 C2 Cl1 . . 119.6(2) ?
C1 C2 Cl1 . . 119.1(2) ?
C4 C3 C2 . . 118.8(3) ?
C4 C3 H3 . . 120.6 ?
C2 C3 H3 . . 120.6 ?
C3 C4 C5 . . 121.6(3) ?
C3 C4 Cl2 . . 118.8(3) ?
C5 C4 Cl2 . . 119.6(3) ?
C4 C5 C6 . . 119.5(3) ?
C4 C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.3 ?
C1 C6 C5 . . 120.7(3) ?
C1 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
O1 C7 C8 . . 111.03(19) ?
O1 C7 H7A . . 109.4 ?
C8 C7 H7A . . 109.4 ?
O1 C7 H7B . . 109.4 ?
C8 C7 H7B . . 109.4 ?
H7A C7 H7B . . 108.0 ?
O2 C8 N1 . . 122.4(2) ?
O2 C8 C7 . . 122.6(2) ?
N1 C8 C7 . . 114.89(19) ?
C8 N1 N1 . 3_676 119.3(2) ?
C8 N1 H1 . . 120.4 ?
N1 N1 H1 3_676 . 120.4 ?
C1 O1 C7 . . 118.22(19) ?
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
C1 O1 . 1.359(3) ?
C1 C6 . 1.386(4) ?
C1 C2 . 1.397(3) ?
C2 C3 . 1.386(4) ?
C2 Cl1 . 1.723(3) ?
C3 C4 . 1.368(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.368(5) ?
C4 Cl2 . 1.742(3) ?
C5 C6 . 1.391(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O1 . 1.419(3) ?
C7 C8 . 1.521(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 O2 . 1.216(3) ?
C8 N1 . 1.329(3) ?
N1 N1 3_676 1.386(4) ?
N1 H1 . 0.8600 ?
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 H1 O2 1_565 0.86 1.94 2.774(3) 163.8 yes

_cod_database_fobs_code 1561634
