#------------------------------------------------------------------------------
#$Date: 2020-04-06 01:12:35 +0300 (Mon, 06 Apr 2020) $
#$Revision: 250392 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/33/2243345.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_2243345
loop_
_publ_author_name
'Daoui, Said'
'Baydere, Cemile'
'Chelfi, Tarik'
'El Kalai, Fouad'
'Dege, Necmi'
'Karrouchi, Khalid'
'Benchat, Noureddine'
_publ_section_title
;
 Polymorphism of
 2-(5-benzyl-6-oxo-3-phenyl-1,6-dihydropyridazin-1-yl)acetic acid with two
 monoclinic modifications: crystal structures and Hirshfeld surface
 analyses
;
_journal_coeditor_code           WM5541
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              432
_journal_page_last               437
_journal_paper_doi               10.1107/S2056989020002406
_journal_volume                  76
_journal_year                    2020
_chemical_formula_moiety         'C19 H16 N2 O3'
_chemical_formula_sum            'C19 H16 N2 O3'
_chemical_formula_weight         320.34
_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-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 109.120(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5976(6)
_cell_length_b                   15.5500(7)
_cell_length_c                   10.3731(7)
_cell_measurement_reflns_used    11065
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.17
_cell_measurement_theta_min      2.03
_cell_volume                     1615.11(17)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2002)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020) and PLATON (Spek, 2020)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), PLATON (Spek, 2020) and publCIF
(Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2017/1 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12114
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.808
_diffrn_reflns_theta_min         2.034
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           45
_diffrn_source_power             2.25
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9657
_exptl_absorpt_correction_T_min  0.9503
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(X-RED32; Stoe & Cie, 2002)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.770
_exptl_crystal_size_mid          0.697
_exptl_crystal_size_min          0.590
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4562
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0487
_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)+(0.0658P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1314
_reflns_number_gt                2560
_reflns_number_total             4562
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5541sup1.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243345
_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.
;
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
O O1 0.72419(10) 0.27629(8) 0.59311(12) 0.0685(3) Uani d 1 . .
O O3 0.85719(10) 0.46576(8) 0.50173(13) 0.0697(3) Uani d 1 . .
O O2 0.97177(11) 0.41088(9) 0.37548(13) 0.0746(4) Uani d 1 . .
H H3 1.024031 0.449746 0.410547 0.112 Uiso calc 1 . .
N N1 0.56525(10) 0.40450(8) 0.30448(12) 0.0469(3) Uani d 1 . .
N N2 0.65255(10) 0.35304(8) 0.39742(12) 0.0482(3) Uani d 1 . .
C C7 0.45128(12) 0.42124(9) 0.32229(14) 0.0448(3) Uani d 1 . .
C C10 0.63572(13) 0.31919(10) 0.51338(15) 0.0505(3) Uani d 1 . .
C C8 0.41953(13) 0.38747(10) 0.43611(15) 0.0518(3) Uani d 1 . .
H H8 0.336938 0.399584 0.445235 0.062 Uiso calc 1 . .
C C6 0.35817(13) 0.47589(9) 0.21629(14) 0.0467(3) Uani d 1 . .
C C9 0.50740(13) 0.33851(10) 0.52997(15) 0.0510(3) Uani d 1 . .
C C12 0.87184(13) 0.41235(11) 0.42288(15) 0.0540(4) Uani d 1 . .
C C11 0.77702(13) 0.33946(10) 0.37033(16) 0.0529(4) Uani d 1 . .
H H11A 0.758711 0.333700 0.272786 0.064 Uiso calc 1 . .
H H11B 0.817891 0.286421 0.413433 0.064 Uiso calc 1 . .
C C14 0.34689(14) 0.30038(11) 0.65991(16) 0.0559(4) Uani d 1 . .
C C1 0.37838(15) 0.48952(12) 0.09292(17) 0.0629(4) Uani d 1 . .
H H1 0.450530 0.463405 0.076387 0.076 Uiso calc 1 . .
C C13 0.48712(15) 0.29980(13) 0.65443(18) 0.0679(5) Uani d 1 . .
H H13A 0.543928 0.330261 0.733863 0.082 Uiso calc 1 . .
H H13B 0.517681 0.240631 0.661889 0.082 Uiso calc 1 . .
C C2 0.29390(17) 0.54093(13) -0.00593(19) 0.0744(5) Uani d 1 . .
H H2 0.309754 0.549564 -0.088011 0.089 Uiso calc 1 . .
C C5 0.25091(17) 0.51563(13) 0.23724(19) 0.0733(5) Uani d 1 . .
H H5 0.234983 0.508074 0.319510 0.088 Uiso calc 1 . .
C C3 0.18788(19) 0.57899(13) 0.0157(2) 0.0814(6) Uani d 1 . .
H H3A 0.129995 0.613227 -0.051425 0.098 Uiso calc 1 . .
C C19 0.3040(2) 0.36098(15) 0.7325(2) 0.0846(6) Uani d 1 . .
H H19 0.361300 0.405216 0.775869 0.102 Uiso calc 1 . .
C C15 0.25885(18) 0.23814(14) 0.5959(2) 0.0837(6) Uani d 1 . .
H H15 0.283752 0.197158 0.543528 0.100 Uiso calc 1 . .
C C17 0.09285(19) 0.29337(18) 0.6803(3) 0.0941(7) Uani d 1 . .
H H17 0.008047 0.290075 0.688145 0.113 Uiso calc 1 . .
C C4 0.1669(2) 0.56655(15) 0.1373(2) 0.0960(7) Uani d 1 . .
H H4 0.094447 0.592977 0.152843 0.115 Uiso calc 1 . .
C C18 0.1777(2) 0.35732(18) 0.7422(3) 0.1008(7) Uani d 1 . .
H H18 0.150476 0.399081 0.791625 0.121 Uiso calc 1 . .
C C16 0.1334(2) 0.23488(17) 0.6074(3) 0.1056(8) Uani d 1 . .
H H16 0.075399 0.191088 0.563708 0.127 Uiso calc 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'
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
C12 O2 H3 . . 109.5 ?
C7 N1 N2 . . 117.63(11) ?
N1 N2 C10 . . 126.35(11) ?
N1 N2 C11 . . 113.56(11) ?
C10 N2 C11 . . 119.97(12) ?
N1 C7 C8 . . 121.48(12) ?
N1 C7 C6 . . 115.55(12) ?
C8 C7 C6 . . 122.96(11) ?
O1 C10 N2 . . 120.56(12) ?
O1 C10 C9 . . 124.76(13) ?
N2 C10 C9 . . 114.67(12) ?
C9 C8 C7 . . 120.84(12) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C5 C6 C1 . . 117.74(14) ?
C5 C6 C7 . . 121.72(13) ?
C1 C6 C7 . . 120.53(12) ?
C8 C9 C10 . . 118.94(13) ?
C8 C9 C13 . . 126.17(13) ?
C10 C9 C13 . . 114.88(12) ?
O2 C12 O3 . . 124.45(14) ?
O3 C12 C11 . . 123.16(12) ?
O2 C12 C11 . . 112.38(13) ?
N2 C11 C12 . . 111.36(12) ?
N2 C11 H11A . . 109.4 ?
C12 C11 H11A . . 109.4 ?
N2 C11 H11B . . 109.4 ?
C12 C11 H11B . . 109.4 ?
H11A C11 H11B . . 108.0 ?
C15 C14 C19 . . 117.36(16) ?
C15 C14 C13 . . 120.40(17) ?
C19 C14 C13 . . 122.19(17) ?
C2 C1 C6 . . 121.30(14) ?
C2 C1 H1 . . 119.4 ?
C6 C1 H1 . . 119.4 ?
C9 C13 C14 . . 116.80(13) ?
C9 C13 H13A . . 108.1 ?
C14 C13 H13A . . 108.1 ?
C9 C13 H13B . . 108.1 ?
C14 C13 H13B . . 108.1 ?
H13A C13 H13B . . 107.3 ?
C3 C2 C1 . . 120.27(16) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
C6 C5 C4 . . 120.37(16) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C2 C3 C4 . . 119.18(17) ?
C2 C3 H3A . . 120.4 ?
C4 C3 H3A . . 120.4 ?
C14 C19 C18 . . 121.1(2) ?
C14 C19 H19 . . 119.5 ?
C18 C19 H19 . . 119.5 ?
C14 C15 C16 . . 120.9(2) ?
C14 C15 H15 . . 119.6 ?
C16 C15 H15 . . 119.6 ?
C16 C17 C18 . . 118.69(19) ?
C16 C17 H17 . . 120.7 ?
C18 C17 H17 . . 120.7 ?
C3 C4 C5 . . 121.14(16) ?
C3 C4 H4 . . 119.4 ?
C5 C4 H4 . . 119.4 ?
C17 C18 C19 . . 120.5(2) ?
C17 C18 H18 . . 119.8 ?
C19 C18 H18 . . 119.8 ?
C17 C16 C15 . . 121.5(2) ?
C17 C16 H16 . . 119.3 ?
C15 C16 H16 . . 119.3 ?
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 . 1.2249(17) ?
O3 C12 . 1.2108(18) ?
O2 C12 . 1.3057(16) ?
O2 H3 . 0.8200 ?
N1 C7 . 1.3064(16) ?
N1 N2 . 1.3570(16) ?
N2 C10 . 1.3771(18) ?
N2 C11 . 1.4513(17) ?
C7 C8 . 1.4294(19) ?
C7 C6 . 1.4813(19) ?
C10 C9 . 1.4568(19) ?
C8 C9 . 1.342(2) ?
C8 H8 . 0.9300 ?
C6 C5 . 1.372(2) ?
C6 C1 . 1.381(2) ?
C9 C13 . 1.502(2) ?
C12 C11 . 1.494(2) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C14 C15 . 1.357(2) ?
C14 C19 . 1.373(3) ?
C14 C13 . 1.506(2) ?
C1 C2 . 1.375(2) ?
C1 H1 . 0.9300 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C2 C3 . 1.352(2) ?
C2 H2 . 0.9300 ?
C5 C4 . 1.375(3) ?
C5 H5 . 0.9300 ?
C3 C4 . 1.364(3) ?
C3 H3A . 0.9300 ?
C19 C18 . 1.376(3) ?
C19 H19 . 0.9300 ?
C15 C16 . 1.374(3) ?
C15 H15 . 0.9300 ?
C17 C16 . 1.340(4) ?
C17 C18 . 1.354(3) ?
C17 H17 . 0.9300 ?
C4 H4 . 0.9300 ?
C18 H18 . 0.9300 ?
C16 H16 . 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
C11 H11B O1 . 0.97 2.39 2.7325(19) 100.3 yes
O2 H3 O3 3_766 0.82 1.84 2.6599(16) 176.9 yes
C5 H5 O3 3_666 0.93 2.40 3.280(2) 158.6 yes
C11 H11A O1 4_565 0.97 2.47 3.2814(19) 141.4 yes

_cod_database_fobs_code 2243345
