#------------------------------------------------------------------------------
#$Date: 2021-02-13 08:11:23 +0200 (Sat, 13 Feb 2021) $
#$Revision: 261939 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/37/2243748.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_2243748
loop_
_publ_author_name
'Mohamed, Shaaban K.'
'Mague, Joel T.'
'Akkurt, Mehmet'
'Albayati, Mustafa R.'
'Elgarhy, Sahar M. I.'
'Al-Taifi, Elham A.'
_publ_section_title
;
 Crystal structures of two hydrazide derivatives of mefenamic acid,
 3-(2,3-dimethylanilino)-N'-[(E)-(furan-2-yl)methylidene]benzohydrazide
 and
 N'-[(E)-benzylidene]-2-(2,3-dimethylanilino)benzohydrazide
;
_journal_coeditor_code           WM5599
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              242
_journal_page_last               246
_journal_paper_doi               10.1107/S2056989021001353
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C20 H19 N3 O2'
_chemical_formula_moiety         'C20 H19 N3 O2'
_chemical_formula_sum            'C20 H19 N3 O2'
_chemical_formula_weight         333.38
_chemical_name_systematic
3-(2,3-Dimethylanilino)-N'-[(E)-(furan-2-yl)methylidene]benzohydrazide
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 104.8140(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8467(3)
_cell_length_b                   15.8409(3)
_cell_length_c                   8.0225(2)
_cell_measurement_reflns_used    9755
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.5232
_cell_measurement_theta_min      3.3015
_cell_volume                     1701.20(7)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT  (Bruker, 2016)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2016/6  (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13222
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         74.516
_diffrn_reflns_theta_min         3.301
_diffrn_source                   'INCOATEC I\mS micro--focus source'
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.189
_refine_ls_extinction_coef       0.0049(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL 2016/6 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         3372
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0363
_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)+(0.0475P)²+0.3981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0951
_reflns_number_gt                2939
_reflns_number_total             3372
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5599sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243748
_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   0.881
_shelx_estimated_absorpt_t_max   0.951
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 0.43892(6) 0.33178(5) 0.45837(10) 0.0275(2) Uani d 1 . .
O O2 0.10644(7) 0.20592(6) 0.31256(12) 0.0371(2) Uani d 1 . .
N N1 0.62923(8) 0.38535(8) 0.58252(15) 0.0353(3) Uani d 1 . .
H H1 0.5810(13) 0.3629(11) 0.495(2) 0.051(5) Uiso d 1 . .
N N2 0.37222(7) 0.26862(7) 0.65665(13) 0.0262(2) Uani d 1 . .
H H2 0.3836(12) 0.2485(11) 0.763(2) 0.043(4) Uiso d 1 . .
N N3 0.29029(7) 0.24278(6) 0.52997(12) 0.0260(2) Uani d 1 . .
C C1 0.70907(9) 0.42610(8) 0.53437(15) 0.0279(3) Uani d 1 . .
C C2 0.76645(9) 0.37935(8) 0.44626(15) 0.0276(3) Uani d 1 . .
C C3 0.84199(9) 0.42133(9) 0.39033(15) 0.0313(3) Uani d 1 . .
C C4 0.85989(10) 0.50619(9) 0.42738(17) 0.0361(3) Uani d 1 . .
H H4 0.9119(12) 0.5334(11) 0.389(2) 0.047(5) Uiso d 1 . .
C C5 0.80281(11) 0.55168(9) 0.51433(19) 0.0378(3) Uani d 1 . .
H H5 0.8130(13) 0.6122(12) 0.533(2) 0.052(5) Uiso d 1 . .
C C6 0.72631(10) 0.51191(9) 0.56546(18) 0.0342(3) Uani d 1 . .
H H6 0.6815(13) 0.5435(11) 0.618(2) 0.052(5) Uiso d 1 . .
C C7 0.74397(12) 0.28753(9) 0.40596(19) 0.0381(3) Uani d 1 . .
H H7A 0.6963(16) 0.2816(13) 0.295(3) 0.073(6) Uiso d 1 . .
H H7B 0.8049(17) 0.2542(14) 0.398(3) 0.078(6) Uiso d 1 . .
H H7C 0.7169(13) 0.2599(12) 0.493(2) 0.055(5) Uiso d 1 . .
C C8 0.90166(13) 0.37716(12) 0.2834(2) 0.0470(4) Uani d 1 . .
H H8A 0.8587(14) 0.3622(12) 0.170(3) 0.056(5) Uiso d 1 . .
H H8B 0.957(2) 0.4145(17) 0.265(3) 0.105(8) Uiso d 1 . .
H H8C 0.9298(16) 0.3242(15) 0.331(3) 0.075(6) Uiso d 1 . .
C C9 0.60374(9) 0.39480(8) 0.73618(15) 0.0275(3) Uani d 1 . .
C C10 0.66889(10) 0.43330(8) 0.88024(16) 0.0326(3) Uani d 1 . .
H H10 0.7324(13) 0.4574(11) 0.866(2) 0.045(4) Uiso d 1 . .
C C11 0.64394(10) 0.44053(9) 1.03499(16) 0.0350(3) Uani d 1 . .
H H11 0.6916(11) 0.4702(10) 1.131(2) 0.037(4) Uiso d 1 . .
C C12 0.55432(10) 0.40856(9) 1.05579(16) 0.0343(3) Uani d 1 . .
H H12 0.5341(11) 0.4161(10) 1.165(2) 0.037(4) Uiso d 1 . .
C C13 0.48990(10) 0.36959(8) 0.91722(16) 0.0293(3) Uani d 1 . .
H H13 0.4250(12) 0.3490(10) 0.9272(19) 0.038(4) Uiso d 1 . .
C C14 0.51281(9) 0.36090(7) 0.75761(15) 0.0251(3) Uani d 1 . .
C C15 0.44003(8) 0.32000(7) 0.61193(14) 0.0238(2) Uani d 1 . .
C C16 0.23183(9) 0.19224(8) 0.58218(15) 0.0280(3) Uani d 1 . .
H H16 0.2460(11) 0.1729(10) 0.701(2) 0.038(4) Uiso d 1 . .
C C17 0.13770(9) 0.16726(8) 0.46938(16) 0.0297(3) Uani d 1 . .
C C18 0.06614(11) 0.11334(10) 0.4926(2) 0.0410(3) Uani d 1 . .
H H18 0.0716(14) 0.0788(12) 0.597(2) 0.059(5) Uiso d 1 . .
C C19 -0.01455(11) 0.11896(10) 0.3418(2) 0.0440(4) Uani d 1 . .
H H19 -0.0782(15) 0.0886(12) 0.319(2) 0.061(5) Uiso d 1 . .
C C20 0.01305(10) 0.17477(10) 0.2391(2) 0.0425(4) Uani d 1 . .
H H20 -0.0217(15) 0.1968(13) 0.124(3) 0.063(5) Uiso 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'
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
C17 O2 C20 . . 106.08(11) ?
C9 N1 C1 . . 126.32(11) ?
C9 N1 H1 . . 115.6(11) ?
C1 N1 H1 . . 115.8(11) ?
C15 N2 N3 . . 118.53(10) ?
C15 N2 H2 . . 120.4(11) ?
N3 N2 H2 . . 120.9(11) ?
C16 N3 N2 . . 114.45(10) ?
C6 C1 C2 . . 120.85(11) ?
C6 C1 N1 . . 120.43(11) ?
C2 C1 N1 . . 118.62(11) ?
C1 C2 C3 . . 118.33(11) ?
C1 C2 C7 . . 120.39(11) ?
C3 C2 C7 . . 121.21(12) ?
C4 C3 C2 . . 119.82(12) ?
C4 C3 C8 . . 118.60(13) ?
C2 C3 C8 . . 121.53(13) ?
C5 C4 C3 . . 121.32(12) ?
C5 C4 H4 . . 120.2(10) ?
C3 C4 H4 . . 118.5(10) ?
C6 C5 C4 . . 119.50(13) ?
C6 C5 H5 . . 119.7(10) ?
C4 C5 H5 . . 120.7(10) ?
C5 C6 C1 . . 120.11(13) ?
C5 C6 H6 . . 121.1(11) ?
C1 C6 H6 . . 118.7(11) ?
C2 C7 H7A . . 110.2(13) ?
C2 C7 H7B . . 112.8(13) ?
H7A C7 H7B . . 106.1(17) ?
C2 C7 H7C . . 112.1(11) ?
H7A C7 H7C . . 108.4(16) ?
H7B C7 H7C . . 106.9(17) ?
C3 C8 H8A . . 110.5(11) ?
C3 C8 H8B . . 111.0(15) ?
H8A C8 H8B . . 108.1(18) ?
C3 C8 H8C . . 113.8(13) ?
H8A C8 H8C . . 104.2(17) ?
H8B C8 H8C . . 108.9(19) ?
N1 C9 C10 . . 121.67(11) ?
N1 C9 C14 . . 120.45(11) ?
C10 C9 C14 . . 117.77(11) ?
C11 C10 C9 . . 121.32(12) ?
C11 C10 H10 . . 120.6(10) ?
C9 C10 H10 . . 118.0(10) ?
C10 C11 C12 . . 121.07(12) ?
C10 C11 H11 . . 118.0(9) ?
C12 C11 H11 . . 120.9(9) ?
C13 C12 C11 . . 118.64(12) ?
C13 C12 H12 . . 119.6(9) ?
C11 C12 H12 . . 121.7(9) ?
C12 C13 C14 . . 121.92(12) ?
C12 C13 H13 . . 120.1(9) ?
C14 C13 H13 . . 118.0(9) ?
C13 C14 C9 . . 119.23(11) ?
C13 C14 C15 . . 119.71(11) ?
C9 C14 C15 . . 121.00(10) ?
O1 C15 N2 . . 121.19(10) ?
O1 C15 C14 . . 123.33(10) ?
N2 C15 C14 . . 115.47(10) ?
N3 C16 C17 . . 120.80(11) ?
N3 C16 H16 . . 122.0(9) ?
C17 C16 H16 . . 117.0(9) ?
C18 C17 O2 . . 109.77(12) ?
C18 C17 C16 . . 131.50(13) ?
O2 C17 C16 . . 118.59(11) ?
C17 C18 C19 . . 106.60(14) ?
C17 C18 H18 . . 124.4(11) ?
C19 C18 H18 . . 129.0(11) ?
C20 C19 C18 . . 106.30(13) ?
C20 C19 H19 . . 126.7(11) ?
C18 C19 H19 . . 127.0(11) ?
C19 C20 O2 . . 111.25(13) ?
C19 C20 H20 . . 131.6(12) ?
O2 C20 H20 . . 117.1(12) ?
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 C15 . 1.2422(14) ?
O2 C17 . 1.3663(16) ?
O2 C20 . 1.3687(16) ?
N1 C9 . 1.3744(16) ?
N1 C1 . 1.4165(16) ?
N1 H1 . 0.910(19) ?
N2 C15 . 1.3582(15) ?
N2 N3 . 1.3777(13) ?
N2 H2 . 0.883(18) ?
N3 C16 . 1.2826(16) ?
C1 C6 . 1.3915(18) ?
C1 C2 . 1.4023(17) ?
C2 C3 . 1.4063(17) ?
C2 C7 . 1.5053(18) ?
C3 C4 . 1.385(2) ?
C3 C8 . 1.507(2) ?
C4 C5 . 1.383(2) ?
C4 H4 . 0.955(17) ?
C5 C6 . 1.3818(19) ?
C5 H5 . 0.975(19) ?
C6 H6 . 0.976(18) ?
C7 H7A . 0.97(2) ?
C7 H7B . 1.01(2) ?
C7 H7C . 0.978(19) ?
C8 H8A . 0.98(2) ?
C8 H8B . 1.01(3) ?
C8 H8C . 0.96(2) ?
C9 C10 . 1.4102(17) ?
C9 C14 . 1.4191(17) ?
C10 C11 . 1.3759(19) ?
C10 H10 . 0.993(17) ?
C11 C12 . 1.389(2) ?
C11 H11 . 0.996(16) ?
C12 C13 . 1.3804(18) ?
C12 H12 . 0.989(16) ?
C13 C14 . 1.4024(17) ?
C13 H13 . 0.978(16) ?
C14 C15 . 1.4829(15) ?
C16 C17 . 1.4392(17) ?
C16 H16 . 0.973(16) ?
C17 C18 . 1.3566(19) ?
C18 C19 . 1.424(2) ?
C18 H18 . 0.990(19) ?
C19 C20 . 1.330(2) ?
C19 H19 . 0.98(2) ?
C20 H20 . 0.99(2) ?
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
N1 H1 O1 . 0.910(19) 1.977(18) 2.7045(14) 135.8(15)
N2 H2 O1 4_566 0.883(18) 2.014(18) 2.8458(13) 156.4(15)
C4 H4 Cg1 2_655 0.955(17) 2.941(17) 3.7248(15) 140.1(17)
C6 H6 O1 3_666 0.976(18) 2.556(18) 3.3434(16) 137.7(14)
C11 H11 Cg2 1_556 0.996(16) 2.765(16) 3.6231(14) 144.8(12)
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
C15 N2 N3 C16 . . . . 177.81(11) ?
C9 N1 C1 C6 . . . . -44.52(19) ?
C9 N1 C1 C2 . . . . 139.08(13) ?
C6 C1 C2 C3 . . . . 0.10(18) ?
N1 C1 C2 C3 . . . . 176.49(11) ?
C6 C1 C2 C7 . . . . -177.09(12) ?
N1 C1 C2 C7 . . . . -0.70(18) ?
C1 C2 C3 C4 . . . . 1.90(18) ?
C7 C2 C3 C4 . . . . 179.07(12) ?
C1 C2 C3 C8 . . . . -175.36(12) ?
C7 C2 C3 C8 . . . . 1.81(19) ?
C2 C3 C4 C5 . . . . -1.98(19) ?
C8 C3 C4 C5 . . . . 175.36(13) ?
C3 C4 C5 C6 . . . . 0.0(2) ?
C4 C5 C6 C1 . . . . 2.0(2) ?
C2 C1 C6 C5 . . . . -2.09(19) ?
N1 C1 C6 C5 . . . . -178.41(12) ?
C1 N1 C9 C10 . . . . -14.2(2) ?
C1 N1 C9 C14 . . . . 169.88(12) ?
N1 C9 C10 C11 . . . . -178.26(12) ?
C14 C9 C10 C11 . . . . -2.20(19) ?
C9 C10 C11 C12 . . . . 1.3(2) ?
C10 C11 C12 C13 . . . . -0.4(2) ?
C11 C12 C13 C14 . . . . 0.5(2) ?
C12 C13 C14 C9 . . . . -1.49(19) ?
C12 C13 C14 C15 . . . . -178.79(12) ?
N1 C9 C14 C13 . . . . 178.37(11) ?
C10 C9 C14 C13 . . . . 2.26(17) ?
N1 C9 C14 C15 . . . . -4.36(18) ?
C10 C9 C14 C15 . . . . 179.53(11) ?
N3 N2 C15 O1 . . . . -12.62(17) ?
N3 N2 C15 C14 . . . . 166.53(10) ?
C13 C14 C15 O1 . . . . 157.42(11) ?
C9 C14 C15 O1 . . . . -19.84(18) ?
C13 C14 C15 N2 . . . . -21.70(16) ?
C9 C14 C15 N2 . . . . 161.04(11) ?
N2 N3 C16 C17 . . . . 173.06(11) ?
C20 O2 C17 C18 . . . . 0.28(15) ?
C20 O2 C17 C16 . . . . -175.78(12) ?
N3 C16 C17 C18 . . . . 177.42(14) ?
N3 C16 C17 O2 . . . . -7.54(18) ?
O2 C17 C18 C19 . . . . -0.22(16) ?
C16 C17 C18 C19 . . . . 175.15(13) ?
C17 C18 C19 C20 . . . . 0.08(17) ?
C18 C19 C20 O2 . . . . 0.10(18) ?
C17 O2 C20 C19 . . . . -0.23(16) ?

_cod_database_fobs_code 2243748
