#------------------------------------------------------------------------------
#$Date: 2019-12-27 19:45:55 +0200 (Fri, 27 Dec 2019) $
#$Revision: 246230 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/19/2311989.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_2311989
loop_
_publ_author_name
'Dammene Debbih, Ouafa'
'Sid, Assia'
'Bouchene, Rafika'
'Bouacida, Sofiane'
'Mazouz, Wissam'
'Gherraf, Noureddine'
_publ_section_title
;
 Two hydrazones derived from 1-aryl-3-(p-substituted
 phenyl)prop-2-en-1-one: synthesis, crystal structure, Hirshfeld surface
 analysis and in vitro biological properties.
;
_journal_coeditor_code           FN3262
_journal_issue                   'Pt 6'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              703
_journal_page_last               714
_journal_paper_doi               10.1107/S2053229618006812
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C25 H17 Cl1 N4 O4'
_chemical_formula_moiety         'C25 H17 Cl1 N4 O4'
_chemical_formula_sum            'C25 H17 Cl N4 O4'
_chemical_formula_weight         472.88
_chemical_name_systematic
(Z)-1-[(E)-3-(4-Chlorophenyl)-1-(naphthalen-1-yl)allylidene]-2-(2,4-dinitrophenyl)hydrazine
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 100.571(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3922(4)
_cell_length_b                   20.9233(14)
_cell_length_c                   14.7828(9)
_cell_measurement_reflns_used    2922
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.61
_cell_measurement_theta_min      2.4
_cell_volume                     2247.6(2)
_computing_cell_refinement
;
APEX2 (Bruker, 2011)
;
_computing_data_collection
;
APEX2 (Bruker, 2011)
;
_computing_data_reduction
;
APEX2 (Bruker, 2011)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt,
2001)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and CRYSCAL (T. Roisnel, local program)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008) and SIR2002 program (Burla et al.,
2005)
;
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12563
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         2.8
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2002)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.283
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0525
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0932P)²+0.1167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1418
_refine_ls_wR_factor_ref         0.1665
_reflns_number_gt                2340
_reflns_number_total             3780
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            fn3262sup1.cif
_cod_data_source_block           H2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2311989
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cl Cl1 0.93794(14) 0.84936(4) 0.40527(7) 0.1075(4) Uani d . 1 1
N N2 0.7184(3) 0.37627(9) 0.58667(14) 0.0560(6) Uani d . 1 1
H H2A 0.7441 0.3749 0.6458 0.067 Uiso calc R 1 1
N N1 0.7413(3) 0.43191(9) 0.54119(14) 0.0552(6) Uani d . 1 1
O O1 0.7676(4) 0.29844(11) 0.72685(13) 0.0965(8) Uani d . 1 1
O O3 0.4168(4) 0.11197(11) 0.42511(17) 0.1062(8) Uani d . 1 1
C C32 0.6412(3) 0.26362(11) 0.58022(16) 0.0501(6) Uani d . 1 1
C C3 0.8611(3) 0.59650(11) 0.58416(17) 0.0534(6) Uani d . 1 1
H H3 0.8831 0.5973 0.6481 0.064 Uiso calc R 1 1
C C30 0.6663(3) 0.50137(10) 0.73798(16) 0.0497(6) Uani d . 1 1
C C34 0.5100(3) 0.21718(11) 0.43665(18) 0.0541(6) Uani d . 1 1
C C2 0.8146(4) 0.54067(12) 0.54467(18) 0.0574(7) Uani d . 1 1
H H2 0.7970 0.5390 0.4808 0.069 Uiso calc R 1 1
C C33 0.5674(3) 0.21077(12) 0.52979(18) 0.0542(6) Uani d . 1 1
H H33 0.5571 0.1718 0.5586 0.065 Uiso calc R 1 1
C C11 0.8817(3) 0.65724(11) 0.53786(17) 0.0500(6) Uani d . 1 1
C C29 0.4982(3) 0.52450(12) 0.68715(19) 0.0581(7) Uani d . 1 1
H H29 0.4791 0.5246 0.6232 0.070 Uiso calc R 1 1
O O2 0.6936(4) 0.20011(11) 0.70958(14) 0.1084(9) Uani d . 1 1
C C22 0.9691(4) 0.45568(13) 0.7485(2) 0.0687(8) Uani d . 1 1
H H22 1.0642 0.4412 0.7205 0.082 Uiso calc R 1 1
C C25 0.6898(4) 0.50055(12) 0.83553(17) 0.0607(7) Uani d . 1 1
N N3 0.7035(4) 0.25359(12) 0.67784(15) 0.0708(7) Uani d . 1 1
C C36 0.5963(3) 0.32661(12) 0.44216(17) 0.0561(7) Uani d . 1 1
H H36 0.6073 0.3649 0.4117 0.067 Uiso calc R 1 1
C C31 0.6550(3) 0.32353(11) 0.53817(16) 0.0460(6) Uani d . 1 1
C C13 0.8484(4) 0.72431(14) 0.4028(2) 0.0668(8) Uani d . 1 1
H H13 0.8134 0.7293 0.3395 0.080 Uiso calc R 1 1
C C1 0.7887(3) 0.48140(11) 0.59293(17) 0.0527(6) Uani d . 1 1
C C21 0.8130(3) 0.47949(11) 0.69606(17) 0.0536(6) Uani d . 1 1
C C16 0.9550(4) 0.70994(12) 0.58946(19) 0.0596(7) Uani d . 1 1
H H16 0.9923 0.7055 0.6527 0.072 Uiso calc R 1 1
C C15 0.9739(4) 0.76855(13) 0.5493(2) 0.0661(8) Uani d . 1 1
H H15 1.0229 0.8031 0.5851 0.079 Uiso calc R 1 1
C C14 0.9198(4) 0.77515(12) 0.4565(2) 0.0633(7) Uani d . 1 1
C C26 0.5464(6) 0.52525(15) 0.8769(2) 0.0852(10) Uani d . 1 1
H H26 0.5604 0.5261 0.9407 0.102 Uiso calc R 1 1
N N4 0.4275(4) 0.16207(12) 0.3849(2) 0.0766(7) Uani d . 1 1
C C35 0.5235(4) 0.27449(12) 0.39261(18) 0.0590(7) Uani d . 1 1
H H35 0.4834 0.2777 0.3294 0.071 Uiso calc R 1 1
O O4 0.3693(4) 0.16852(11) 0.30282(18) 0.1181(10) Uani d . 1 1
C C12 0.8288(4) 0.66594(13) 0.44310(18) 0.0596(7) Uani d . 1 1
H H12 0.7794 0.6318 0.4065 0.072 Uiso calc R 1 1
C C28 0.3648(4) 0.54648(14) 0.7308(3) 0.0786(9) Uani d . 1 1
H H28 0.2545 0.5610 0.6963 0.094 Uiso calc R 1 1
C C23 0.9876(5) 0.45285(15) 0.8457(3) 0.0900(11) Uani d . 1 1
H H23 1.0936 0.4358 0.8812 0.108 Uiso calc R 1 1
C C27 0.3896(6) 0.54761(15) 0.8252(3) 0.0947(12) Uani d . 1 1
H H27 0.2974 0.5640 0.8538 0.114 Uiso calc R 1 1
C C24 0.8503(6) 0.47504(16) 0.8864(2) 0.0831(10) Uani d . 1 1
H H24 0.8638 0.4732 0.9502 0.100 Uiso calc R 1 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 0 '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 0.006 '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
C31 N2 N1 119.68(19)
C31 N2 H2A 120.2
N1 N2 H2A 120.2
C1 N1 N2 115.7(2)
C33 C32 C31 121.6(2)
C33 C32 N3 116.2(2)
C31 C32 N3 122.2(2)
C2 C3 C11 126.9(2)
C2 C3 H3 116.5
C11 C3 H3 116.5
C29 C30 C21 123.1(2)
C29 C30 C25 118.4(2)
C21 C30 C25 118.6(2)
C33 C34 C35 121.6(2)
C33 C34 N4 118.3(2)
C35 C34 N4 120.1(2)
C3 C2 C1 125.5(2)
C3 C2 H2 117.2
C1 C2 H2 117.2
C34 C33 C32 118.7(2)
C34 C33 H33 120.6
C32 C33 H33 120.6
C16 C11 C12 117.1(2)
C16 C11 C3 119.6(2)
C12 C11 C3 123.2(2)
C28 C29 C30 120.6(3)
C28 C29 H29 119.7
C30 C29 H29 119.7
C21 C22 C23 120.4(3)
C21 C22 H22 119.8
C23 C22 H22 119.8
C24 C25 C26 122.6(3)
C24 C25 C30 119.2(3)
C26 C25 C30 118.2(3)
O2 N3 O1 121.2(2)
O2 N3 C32 119.1(2)
O1 N3 C32 119.7(2)
C35 C36 C31 121.4(2)
C35 C36 H36 119.3
C31 C36 H36 119.3
N2 C31 C36 120.7(2)
N2 C31 C32 122.5(2)
C36 C31 C32 116.8(2)
C14 C13 C12 119.8(3)
C14 C13 H13 120.1
C12 C13 H13 120.1
N1 C1 C2 115.8(2)
N1 C1 C21 123.1(2)
C2 C1 C21 121.1(2)
C22 C21 C30 120.3(2)
C22 C21 C1 121.2(2)
C30 C21 C1 118.4(2)
C15 C16 C11 121.8(3)
C15 C16 H16 119.1
C11 C16 H16 119.1
C14 C15 C16 119.3(3)
C14 C15 H15 120.4
C16 C15 H15 120.4
C15 C14 C13 120.9(3)
C15 C14 Cl1 119.7(2)
C13 C14 Cl1 119.4(2)
C27 C26 C25 121.0(3)
C27 C26 H26 119.5
C25 C26 H26 119.5
O3 N4 O4 122.7(3)
O3 N4 C34 119.0(3)
O4 N4 C34 118.3(3)
C36 C35 C34 119.8(2)
C36 C35 H35 120.1
C34 C35 H35 120.1
C13 C12 C11 121.1(2)
C13 C12 H12 119.4
C11 C12 H12 119.4
C29 C28 C27 121.1(3)
C29 C28 H28 119.5
C27 C28 H28 119.5
C24 C23 C22 119.7(3)
C24 C23 H23 120.2
C22 C23 H23 120.2
C26 C27 C28 120.7(3)
C26 C27 H27 119.7
C28 C27 H27 119.7
C23 C24 C25 121.7(3)
C23 C24 H24 119.1
C25 C24 H24 119.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C14 1.743(3)
N2 C31 1.352(3)
N2 N1 1.370(3)
N2 H2A 0.8600
N1 C1 1.297(3)
O1 N3 1.226(3)
O3 N4 1.215(3)
C32 C33 1.388(3)
C32 C31 1.411(3)
C32 N3 1.447(3)
C3 C2 1.323(3)
C3 C11 1.465(3)
C3 H3 0.9300
C30 C29 1.415(3)
C30 C21 1.420(3)
C30 C25 1.421(3)
C34 C33 1.371(3)
C34 C35 1.377(3)
C34 N4 1.455(3)
C2 C1 1.461(3)
C2 H2 0.9300
C33 H33 0.9300
C11 C16 1.393(3)
C11 C12 1.395(3)
C29 C28 1.354(4)
C29 H29 0.9300
O2 N3 1.221(3)
C22 C21 1.361(4)
C22 C23 1.419(5)
C22 H22 0.9300
C25 C24 1.390(4)
C25 C26 1.415(4)
C36 C35 1.368(3)
C36 C31 1.407(3)
C36 H36 0.9300
C13 C14 1.373(4)
C13 C12 1.378(4)
C13 H13 0.9300
C1 C21 1.503(3)
C16 C15 1.381(4)
C16 H16 0.9300
C15 C14 1.364(4)
C15 H15 0.9300
C26 C27 1.349(5)
C26 H26 0.9300
N4 O4 1.218(3)
C35 H35 0.9300
C12 H12 0.9300
C28 C27 1.374(5)
C28 H28 0.9300
C23 C24 1.354(5)
C23 H23 0.9300
C27 H27 0.9300
C24 H24 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
N2 H2A O1 . 0.8600 1.9900 2.609(3) 128.00 yes
N2 H2A N3 . 0.8600 2.6100 2.911(3) 102.00 yes
C23 H23 O3 4_666 0.9300 2.5600 3.452(4) 160.00 yes
C36 H36 N1 . 0.9300 2.4300 2.751(3) 100.00 yes
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
C31 N2 N1 C1 174.8(2)
C11 C3 C2 C1 -177.6(2)
C35 C34 C33 C32 -0.1(4)
N4 C34 C33 C32 -178.1(2)
C31 C32 C33 C34 1.2(4)
N3 C32 C33 C34 -178.6(2)
C2 C3 C11 C16 -171.5(3)
C2 C3 C11 C12 9.3(4)
C21 C30 C29 C28 -178.1(2)
C25 C30 C29 C28 1.3(4)
C29 C30 C25 C24 176.8(2)
C21 C30 C25 C24 -3.7(3)
C29 C30 C25 C26 -2.4(3)
C21 C30 C25 C26 177.0(2)
C33 C32 N3 O2 2.2(4)
C31 C32 N3 O2 -177.6(2)
C33 C32 N3 O1 -178.9(3)
C31 C32 N3 O1 1.4(4)
N1 N2 C31 C36 -5.9(3)
N1 N2 C31 C32 175.2(2)
C35 C36 C31 N2 -176.8(2)
C35 C36 C31 C32 2.2(4)
C33 C32 C31 N2 176.8(2)
N3 C32 C31 N2 -3.4(4)
C33 C32 C31 C36 -2.2(3)
N3 C32 C31 C36 177.6(2)
N2 N1 C1 C2 179.6(2)
N2 N1 C1 C21 -1.5(3)
C3 C2 C1 N1 179.3(3)
C3 C2 C1 C21 0.4(4)
C23 C22 C21 C30 -0.5(4)
C23 C22 C21 C1 -178.5(2)
C29 C30 C21 C22 -177.7(2)
C25 C30 C21 C22 2.9(3)
C29 C30 C21 C1 0.4(3)
C25 C30 C21 C1 -179.1(2)
N1 C1 C21 C22 79.5(3)
C2 C1 C21 C22 -101.7(3)
N1 C1 C21 C30 -98.5(3)
C2 C1 C21 C30 80.3(3)
C12 C11 C16 C15 0.5(4)
C3 C11 C16 C15 -178.7(2)
C11 C16 C15 C14 -0.2(4)
C16 C15 C14 C13 -0.4(4)
C16 C15 C14 Cl1 178.5(2)
C12 C13 C14 C15 0.8(4)
C12 C13 C14 Cl1 -178.17(19)
C24 C25 C26 C27 -177.7(3)
C30 C25 C26 C27 1.6(4)
C33 C34 N4 O3 -2.0(4)
C35 C34 N4 O3 -179.9(3)
C33 C34 N4 O4 176.9(3)
C35 C34 N4 O4 -1.1(4)
C31 C36 C35 C34 -1.3(4)
C33 C34 C35 C36 0.2(4)
N4 C34 C35 C36 178.1(2)
C14 C13 C12 C11 -0.5(4)
C16 C11 C12 C13 -0.1(4)
C3 C11 C12 C13 179.0(2)
C30 C29 C28 C27 0.8(4)
C21 C22 C23 C24 -1.2(4)
C25 C26 C27 C28 0.5(5)
C29 C28 C27 C26 -1.7(5)
C22 C23 C24 C25 0.3(5)
C26 C25 C24 C23 -178.6(3)
C30 C25 C24 C23 2.2(4)
