##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2018/3'
_journal_date_recd_electronic     2019-07-04
_journal_date_accepted     2019-08-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2019
_journal_volume     75
_journal_issue      9
_journal_page_first     1352
_journal_page_last     1356
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989019011551
_journal_coeditor_code     MW2146
_publ_contact_author_name     'Said Daoui'
_publ_contact_author_address
;
Depertmant of Physics
Faculty of Arts and Sciences
Ondokuz Mayıs Üniversity
55139 Samsun
Turkey
;
_publ_contact_author_email
        'saiddaoui26@gmail.com, emineberrin.cinar@omu.edu.tr, necmid@omu.edu.tr'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '05313668908'
_publ_section_title
;
Crystal structure and Hirshfeld surface analysis of
4-(4-methylbenzyl)-6-phenylpyridazin-3(2H)-one
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Daoui, Said' .
;
Laboratory of Applied Chemistry and Environment (LCAE)
Department of Chemistry
Faculty of Sciences
University Mohamed Premier
Oujda 60000
Morocco
;
    'Cinar, Emine Berrin' .
;
Ondokuz Mayıs University
Faculty of Arts and Sciences
Department of Physics
Kurupelit
Samsun
Turkey
;
    'El Kali, Fouad' .
;
Laboratory of Applied Chemistry and Environment (LCAE)
Department of Chemistry
Faculty of Sciences
University Mohamed Premier
Oujda 60000
Morocco
;
    'Saddik, Rafik' .
;
Laboratory of Organic Synthesis, Extraction and Development
Faculty of Sciences
Hassan II University
Casablanca
Morocco
;
    'Karrouchi, Khalid' .
;
Laboratory of Plant Chemistry
Organic and Bioorganic Synthesis
URAC23
Faculty of Science
BP 1014
GEOPAC Research Center
Mohammed V University
Rabat
Morocco
;
    'Benchat, Noureddine' .
;
Laboratory of Applied Chemistry and Environment (LCAE)
Department of Chemistry
Faculty of Sciences
University Mohamed Premier
Oujda 60000
Morocco
;
    'Baydere, Cemile' .
;
Ondokuz Mayıs University
Faculty of Arts and Sciences
Department of Physics
Kurupelit
Samsun
Turkey
;
    'Dege, Necmi' .
;
Ondokuz Mayıs University
Faculty of Arts and Sciences
Department of Physics
Kurupelit
Samsun
Turkey
;
_publ_section_synopsis
;
In the title compound, intermolecular N---H...O hydrogen bonds link the
molecules into a three-dimensional supramolecular network.
;
_chemical_name_systematic
;
4-(4-Methylbenzyl)-6-phenylpyridazin-3(2H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H16 N2 O'
_chemical_formula_sum     'C18 H16 N2 O'
_chemical_formula_iupac     'C18 H16 N2 O'
_chemical_formula_weight     276.33
_chemical_melting_point     ?
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     5.8479(5)
_cell_length_b     8.5738(7)
_cell_length_c     15.2439(12)
_cell_angle_alpha     80.693(6)
_cell_angle_beta     83.147(7)
_cell_angle_gamma     78.164(7)
_cell_volume     735.27(11)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     8216
_cell_measurement_theta_min     2.45
_cell_measurement_theta_max     30.67
_cell_measurement_temperature     296(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.270
_exptl_crystal_size_mid     0.197
_exptl_crystal_size_min     0.060
_exptl_crystal_density_diffrn     1.248
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     292
_exptl_absorpt_coefficient_mu     0.079
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details
;
(X-RED32; Stoe & Cie, 2002)
;
_exptl_absorpt_correction_T_min     0.9657
_exptl_absorpt_correction_T_max     0.9958
_diffrn_ambient_temperature     296(2)
_diffrn_source     'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_power     2.25
_diffrn_source_voltage     50
_diffrn_source_current     45
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'plane graphite'
_diffrn_measurement_device_type     'Stoe IPDS 2'
_diffrn_measurement_device     '2-circle goniometer'
_diffrn_measurement_method     'rotation method'
_diffrn_detector     'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean     6.67
_diffrn_reflns_number     9453
_diffrn_reflns_av_R_equivalents     0.0860
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_theta_min     2.452
_diffrn_reflns_theta_max     25.998
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_refine_special_details     ?
_reflns_number_total     2887
_reflns_number_gt     1471
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1366
_refine_ls_R_factor_gt     0.0682
_refine_ls_wR_factor_gt     0.1762
_refine_ls_wR_factor_ref     0.2081
_refine_ls_goodness_of_fit_ref     1.052
_refine_ls_restrained_S_all     1.148
_refine_ls_number_reflns     2887
_refine_ls_number_parameters     191
_refine_ls_number_restraints     84
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0939P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.298
_refine_diff_density_min     -0.323
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
X-AREA (Stoe & Cie, 2002)
;
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_reduction
;
X-RED (Stoe & Cie, 2002)
;
_computing_structure_solution
;
SHELXT2017 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008) and PLATON (Spek, 2009)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), SHELXL2018 (Sheldrick, 2015b),
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;
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
    O O1 0.9692(4) 0.6487(3) 0.90252(15) 0.0776(7) Uani d 1 . .
    N N1 0.7762(4) 0.4423(3) 0.94429(17) 0.0653(7) Uani d 1 . .
    H H1 0.848007 0.419860 0.992137 0.078 Uiso calc 1 . .
    N N2 0.6315(4) 0.3435(3) 0.93530(17) 0.0621(7) Uani d 1 . .
    C C10 0.8227(5) 0.5725(4) 0.8874(2) 0.0627(8) Uani d 1 . .
    C C13 0.3636(6) 0.2661(4) 0.8525(2) 0.0728(8) Uani d 1 . .
    C C11 0.5151(5) 0.3799(4) 0.8641(2) 0.0594(8) Uani d 1 . .
    C C5 0.6414(6) 0.7618(4) 0.6536(2) 0.0668(9) Uani d 1 . .
    C C9 0.6964(5) 0.6101(4) 0.8080(2) 0.0630(8) Uani d 1 . .
    C C12 0.5470(5) 0.5134(4) 0.7992(2) 0.0671(9) Uani d 1 . .
    H H12 0.463050 0.535285 0.749060 0.080 Uiso calc 1 . .
    C C2 0.4368(7) 0.7711(4) 0.4949(2) 0.0738(10) Uani d 1 . .
    C C18 0.2108(6) 0.2984(4) 0.7881(2) 0.0750(8) Uani d 1 . .
    H H18 0.200948 0.394224 0.748873 0.090 Uiso calc 1 . .
    C C3 0.3212(7) 0.8506(5) 0.5622(3) 0.0806(11) Uani d 1 . .
    H H3 0.170292 0.909110 0.555296 0.097 Uiso calc 1 . .
    C C17 0.0695(6) 0.1901(5) 0.7802(3) 0.0812(9) Uani d 1 . .
    H H17 -0.034226 0.214814 0.736029 0.097 Uiso calc 1 . .
    C C8 0.7452(7) 0.7504(4) 0.7414(2) 0.0793(11) Uani d 1 . .
    H H8A 0.913650 0.742443 0.729872 0.095 Uiso calc 1 . .
    H H8B 0.682622 0.848692 0.766918 0.095 Uiso calc 1 . .
    C C16 0.0804(7) 0.0510(5) 0.8351(3) 0.0895(10) Uani d 1 . .
    H H16 -0.016404 -0.019967 0.829942 0.107 Uiso calc 1 . .
    C C4 0.4200(7) 0.8474(4) 0.6402(2) 0.0770(10) Uani d 1 . .
    H H4 0.335386 0.904240 0.684478 0.092 Uiso calc 1 . .
    C C6 0.7593(6) 0.6817(5) 0.5855(3) 0.0819(11) Uani d 1 . .
    H H6 0.910392 0.623176 0.591920 0.098 Uiso calc 1 . .
    C C7 0.6572(7) 0.6867(5) 0.5077(3) 0.0870(11) Uani d 1 . .
    H H7 0.741083 0.631025 0.462885 0.104 Uiso calc 1 . .
    C C1 0.3250(8) 0.7769(6) 0.4096(3) 0.1041(14) Uani d 1 . .
    H H1A 0.164486 0.831458 0.415749 0.156 Uiso calc 1 . .
    H H1B 0.330986 0.669253 0.398093 0.156 Uiso calc 1 . .
    H H1C 0.408494 0.833710 0.360869 0.156 Uiso calc 1 . .
    C C14 0.3757(8) 0.1221(5) 0.9057(3) 0.1055(11) Uani d 1 . .
    H H14 0.482967 0.094249 0.948657 0.127 Uiso calc 1 . .
    C C15 0.2333(8) 0.0152(6) 0.8979(3) 0.1111(11) Uani d 1 . .
    H H15 0.243396 -0.081609 0.936290 0.133 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    O1 C10 . 1.241(3) y
    N1 N2 . 1.347(3) y
    N1 C10 . 1.352(4) y
    N1 H1 . 0.8600 ?
    N2 C11 . 1.311(4) y
    C10 C9 . 1.449(4) ?
    C13 C14 . 1.357(5) ?
    C13 C18 . 1.364(4) ?
    C13 C11 . 1.488(4) ?
    C11 C12 . 1.415(4) ?
    C5 C4 . 1.372(5) ?
    C5 C6 . 1.375(5) ?
    C5 C8 . 1.515(4) ?
    C9 C12 . 1.353(4) ?
    C9 C8 . 1.496(4) ?
    C12 H12 . 0.9300 ?
    C2 C3 . 1.359(5) ?
    C2 C7 . 1.361(5) ?
    C2 C1 . 1.512(5) ?
    C18 C17 . 1.391(4) ?
    C18 H18 . 0.9300 ?
    C3 C4 . 1.378(5) ?
    C3 H3 . 0.9300 ?
    C17 C16 . 1.336(5) ?
    C17 H17 . 0.9300 ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C16 C15 . 1.344(6) ?
    C16 H16 . 0.9300 ?
    C4 H4 . 0.9300 ?
    C6 C7 . 1.381(5) ?
    C6 H6 . 0.9300 ?
    C7 H7 . 0.9300 ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C14 C15 . 1.386(5) ?
    C14 H14 . 0.9300 ?
    C15 H15 . 0.9300 ?
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 C10 . . 128.0(2) ?
    N2 N1 H1 . . 116.0 ?
    C10 N1 H1 . . 116.0 ?
    C11 N2 N1 . . 116.5(3) ?
    O1 C10 N1 . . 120.9(3) y
    O1 C10 C9 . . 123.9(3) y
    N1 C10 C9 . . 115.1(2) ?
    C14 C13 C18 . . 116.8(3) ?
    C14 C13 C11 . . 120.7(3) ?
    C18 C13 C11 . . 122.5(3) ?
    N2 C11 C12 . . 121.3(3) ?
    N2 C11 C13 . . 116.2(3) ?
    C12 C11 C13 . . 122.4(3) ?
    C4 C5 C6 . . 117.0(3) ?
    C4 C5 C8 . . 121.1(4) ?
    C6 C5 C8 . . 121.9(3) ?
    C12 C9 C10 . . 117.4(3) ?
    C12 C9 C8 . . 125.0(3) ?
    C10 C9 C8 . . 117.5(2) y
    C9 C12 C11 . . 121.7(3) ?
    C9 C12 H12 . . 119.1 ?
    C11 C12 H12 . . 119.1 ?
    C3 C2 C7 . . 117.0(3) ?
    C3 C2 C1 . . 121.2(4) ?
    C7 C2 C1 . . 121.8(4) ?
    C13 C18 C17 . . 120.9(4) ?
    C13 C18 H18 . . 119.6 ?
    C17 C18 H18 . . 119.6 ?
    C2 C3 C4 . . 122.2(4) ?
    C2 C3 H3 . . 118.9 ?
    C4 C3 H3 . . 118.9 ?
    C16 C17 C18 . . 121.0(3) ?
    C16 C17 H17 . . 119.5 ?
    C18 C17 H17 . . 119.5 ?
    C9 C8 C5 . . 113.7(2) y
    C9 C8 H8A . . 108.8 ?
    C5 C8 H8A . . 108.8 ?
    C9 C8 H8B . . 108.8 ?
    C5 C8 H8B . . 108.8 ?
    H8A C8 H8B . . 107.7 ?
    C17 C16 C15 . . 119.1(3) ?
    C17 C16 H16 . . 120.5 ?
    C15 C16 H16 . . 120.5 ?
    C5 C4 C3 . . 121.0(4) ?
    C5 C4 H4 . . 119.5 ?
    C3 C4 H4 . . 119.5 ?
    C5 C6 C7 . . 121.1(4) ?
    C5 C6 H6 . . 119.4 ?
    C7 C6 H6 . . 119.4 ?
    C2 C7 C6 . . 121.7(4) ?
    C2 C7 H7 . . 119.1 ?
    C6 C7 H7 . . 119.1 ?
    C2 C1 H1A . . 109.5 ?
    C2 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    C2 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    C13 C14 C15 . . 122.0(4) ?
    C13 C14 H14 . . 119.0 ?
    C15 C14 H14 . . 119.0 ?
    C16 C15 C14 . . 120.1(4) ?
    C16 C15 H15 . . 119.9 ?
    C14 C15 H15 . . 119.9 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C10 N1 N2 C11 . . . . -2.3(5) ?
    N2 N1 C10 O1 . . . . -176.7(3) ?
    N2 N1 C10 C9 . . . . 1.2(5) ?
    N1 N2 C11 C12 . . . . 1.9(5) ?
    N1 N2 C11 C13 . . . . 177.4(3) y
    C14 C13 C11 N2 . . . . -9.6(5) ?
    C18 C13 C11 N2 . . . . 171.6(3) ?
    C14 C13 C11 C12 . . . . 165.7(4) ?
    C18 C13 C11 C12 . . . . -13.0(5) ?
    O1 C10 C9 C12 . . . . 178.0(3) ?
    N1 C10 C9 C12 . . . . 0.2(5) ?
    O1 C10 C9 C8 . . . . -0.7(5) ?
    N1 C10 C9 C8 . . . . -178.5(3) ?
    C10 C9 C12 C11 . . . . -0.4(5) ?
    C8 C9 C12 C11 . . . . 178.2(3) ?
    N2 C11 C12 C9 . . . . -0.7(5) ?
    C13 C11 C12 C9 . . . . -175.9(3) ?
    C14 C13 C18 C17 . . . . 2.2(6) ?
    C11 C13 C18 C17 . . . . -179.0(3) ?
    C7 C2 C3 C4 . . . . 0.1(6) ?
    C1 C2 C3 C4 . . . . -179.7(4) ?
    C13 C18 C17 C16 . . . . -0.4(6) ?
    C12 C9 C8 C5 . . . . -9.4(6) ?
    C10 C9 C8 C5 . . . . 169.2(3) y
    C4 C5 C8 C9 . . . . 90.3(4) y
    C6 C5 C8 C9 . . . . -86.8(4) y
    C18 C17 C16 C15 . . . . -1.0(7) ?
    C6 C5 C4 C3 . . . . 0.7(5) ?
    C8 C5 C4 C3 . . . . -176.5(3) ?
    C2 C3 C4 C5 . . . . -0.5(6) ?
    C4 C5 C6 C7 . . . . -0.6(5) ?
    C8 C5 C6 C7 . . . . 176.6(3) ?
    C3 C2 C7 C6 . . . . 0.0(6) ?
    C1 C2 C7 C6 . . . . 179.9(4) ?
    C5 C6 C7 C2 . . . . 0.2(6) ?
    C18 C13 C14 C15 . . . . -2.7(7) ?
    C11 C13 C14 C15 . . . . 178.5(4) ?
    C17 C16 C15 C14 . . . . 0.5(7) ?
    C13 C14 C15 C16 . . . . 1.4(8) ?
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 O1 2_767 0.86 1.98 2.836(3) 174.8 yes
    C14 H14 N2 . 0.93 2.43 2.764(3) 100.9 yes
_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     ?
_shelx_estimated_absorpt_T_max     ?
