#------------------------------------------------------------------------------
#$Date: 2021-02-05 00:58:51 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261604 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/17/7241774.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7241774
loop_
_publ_author_name
'Ahmed, Muhammad Naeem'
'Arif, Muneeba'
'Andleeb, Hina'
'Ali Shah, Syed Wadood'
'Arshad, Ifzan'
'Tahir, Muhammad Nawaz'
'Rocha, Mariana'
'Gil, Diego M.'
_publ_section_title
;
 Interplay of weak noncovalent interactions in alkoxybenzylidene
 derivatives of benzohydrazide and acetohydrazide: a combined experimental
 and theoretical investigation and lipoxygenase inhibition (LOX) studies
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              955
_journal_page_last               971
_journal_paper_doi               10.1039/D0CE01402H
_journal_volume                  23
_journal_year                    2021
_chemical_formula_iupac          'C18 H20 N2 O3'
_chemical_formula_moiety         'C18 H20 N2 O3'
_chemical_formula_sum            'C18 H20 N2 O3'
_chemical_formula_weight         312.36
_chemical_name_systematic
;
4-Methoxy-N'-[(E)-(2-propoxyphenyl)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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-11-04 deposited with the CCDC.	2020-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.782(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.896(8)
_cell_length_b                   4.9911(17)
_cell_length_c                   13.723(4)
_cell_measurement_reflns_used    2243
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.042
_cell_measurement_theta_min      2.622
_cell_volume                     1596.1(9)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL-2018/3  (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18062
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.042
_diffrn_reflns_theta_min         2.622
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 536 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3836
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1123
_refine_ls_R_factor_gt           0.0581
_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)+(0.0520P)²+0.2291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1382
_reflns_number_gt                2243
_reflns_number_total             3836
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            d0ce01402h2.cif
_cod_data_source_block           MH4AJK
_cod_depositor_comments
'Adding full bibliography for 7241774--7241775.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7241774
_shelx_shelxl_version_number     2018/3
_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   0.967
_shelx_estimated_absorpt_t_max   0.986
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.45411(6) 0.0524(3) 0.08859(11) 0.0579(4) Uani 1 1 d . . . . .
O2 O 0.13528(5) 0.5081(3) 0.48627(9) 0.0400(4) Uani 1 1 d . . . . .
O3 O 0.31563(6) -0.4059(3) 0.39531(10) 0.0500(4) Uani 1 1 d . . . . .
N1 N 0.28663(7) 0.0261(3) 0.39196(12) 0.0396(4) Uani 1 1 d . . . . .
H1 H 0.287893 0.183390 0.366963 0.047 Uiso 1 1 calc R U . . .
N2 N 0.25376(7) -0.0195(3) 0.46112(11) 0.0385(4) Uani 1 1 d . . . . .
C1 C 0.35204(8) -0.1039(4) 0.29044(13) 0.0344(5) Uani 1 1 d . . . . .
C2 C 0.33611(9) 0.0930(4) 0.21920(15) 0.0454(5) Uani 1 1 d . . . . .
H2 H 0.302645 0.189620 0.217619 0.055 Uiso 1 1 calc R U . . .
C3 C 0.36862(9) 0.1504(5) 0.15008(15) 0.0485(6) Uani 1 1 d . . . . .
H3 H 0.356757 0.282457 0.102131 0.058 Uiso 1 1 calc R U . . .
C4 C 0.41842(8) 0.0118(4) 0.15261(14) 0.0411(5) Uani 1 1 d . . . . .
C5 C 0.43537(9) -0.1834(5) 0.22370(16) 0.0523(6) Uani 1 1 d . . . . .
H5 H 0.469446 -0.275959 0.226283 0.063 Uiso 1 1 calc R U . . .
C6 C 0.40223(9) -0.2428(4) 0.29105(16) 0.0491(6) Uani 1 1 d . . . . .
H6 H 0.413736 -0.378247 0.337702 0.059 Uiso 1 1 calc R U . . .
C7 C 0.43977(11) 0.2586(5) 0.01584(17) 0.0631(7) Uani 1 1 d . . . . .
H7A H 0.403074 0.220823 -0.026971 0.095 Uiso 1 1 calc R U . . .
H7B H 0.468401 0.266779 -0.023348 0.095 Uiso 1 1 calc R U . . .
H7C H 0.438157 0.427276 0.048697 0.095 Uiso 1 1 calc R U . . .
C8 C 0.31701(8) -0.1778(4) 0.36336(14) 0.0368(5) Uani 1 1 d . . . . .
C9 C 0.22774(8) 0.1850(4) 0.48445(13) 0.0355(5) Uani 1 1 d . . . . .
H9 H 0.228800 0.345871 0.450703 0.043 Uiso 1 1 calc R U . . .
C10 C 0.19599(8) 0.1678(4) 0.56459(13) 0.0316(4) Uani 1 1 d . . . . .
C11 C 0.21177(8) -0.0167(4) 0.64206(14) 0.0387(5) Uani 1 1 d . . . . .
H11 H 0.240802 -0.139415 0.640197 0.046 Uiso 1 1 calc R U . . .
C12 C 0.18496(9) -0.0203(4) 0.72161(14) 0.0447(5) Uani 1 1 d . . . . .
H12 H 0.195659 -0.145527 0.772518 0.054 Uiso 1 1 calc R U . . .
C13 C 0.14253(9) 0.1618(4) 0.72489(14) 0.0447(5) Uani 1 1 d . . . . .
H13 H 0.125288 0.162733 0.779371 0.054 Uiso 1 1 calc R U . . .
C14 C 0.12497(9) 0.3441(4) 0.64859(14) 0.0407(5) Uani 1 1 d . . . . .
H14 H 0.095792 0.465347 0.651231 0.049 Uiso 1 1 calc R U . . .
C15 C 0.15124(8) 0.3450(4) 0.56778(13) 0.0320(4) Uani 1 1 d . . . . .
C16 C 0.08874(8) 0.6892(4) 0.48332(14) 0.0371(5) Uani 1 1 d . . . . .
H16A H 0.098152 0.816194 0.538010 0.045 Uiso 1 1 calc R U . . .
H16B H 0.054534 0.591767 0.489305 0.045 Uiso 1 1 calc R U . . .
C17 C 0.07869(9) 0.8332(4) 0.38502(15) 0.0460(5) Uani 1 1 d . . . . .
H17A H 0.071300 0.702970 0.331239 0.055 Uiso 1 1 calc R U . . .
H17B H 0.113039 0.931803 0.380686 0.055 Uiso 1 1 calc R U . . .
C18 C 0.02849(10) 1.0259(5) 0.37195(17) 0.0587(6) Uani 1 1 d . . . . .
H18A H -0.005912 0.928113 0.373379 0.088 Uiso 1 1 calc R U . . .
H18B H 0.024022 1.116761 0.309025 0.088 Uiso 1 1 calc R U . . .
H18C H 0.035577 1.154927 0.425159 0.088 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C7 118.07(17) . . ?
C15 O2 C16 118.35(14) . . ?
C8 N1 N2 119.88(16) . . ?
C8 N1 H1 120.1 . . ?
N2 N1 H1 120.1 . . ?
C9 N2 N1 115.20(16) . . ?
C2 C1 C6 117.66(18) . . ?
C2 C1 C8 123.09(17) . . ?
C6 C1 C8 119.22(18) . . ?
C1 C2 C3 121.69(19) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 119.64(19) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
O1 C4 C3 124.76(19) . . ?
O1 C4 C5 115.67(18) . . ?
C3 C4 C5 119.58(18) . . ?
C4 C5 C6 120.42(19) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 121.0(2) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 C8 N1 122.38(18) . . ?
O3 C8 C1 122.43(18) . . ?
N1 C8 C1 115.19(17) . . ?
N2 C9 C10 120.22(18) . . ?
N2 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C15 118.33(17) . . ?
C11 C10 C9 120.78(18) . . ?
C15 C10 C9 120.82(17) . . ?
C12 C11 C10 121.09(19) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C11 119.53(19) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 121.02(18) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 119.49(19) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
O2 C15 C14 124.12(17) . . ?
O2 C15 C10 115.37(15) . . ?
C14 C15 C10 120.49(17) . . ?
O2 C16 C17 107.32(15) . . ?
O2 C16 H16A 110.3 . . ?
C17 C16 H16A 110.3 . . ?
O2 C16 H16B 110.3 . . ?
C17 C16 H16B 110.3 . . ?
H16A C16 H16B 108.5 . . ?
C16 C17 C18 112.04(17) . . ?
C16 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.368(2) . ?
O1 C7 1.422(3) . ?
O2 C15 1.368(2) . ?
O2 C16 1.427(2) . ?
O3 C8 1.223(2) . ?
N1 C8 1.357(2) . ?
N1 N2 1.378(2) . ?
N1 H1 0.8600 . ?
N2 C9 1.272(2) . ?
C1 C2 1.379(3) . ?
C1 C6 1.384(3) . ?
C1 C8 1.486(3) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(3) . ?
C5 C6 1.376(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 C10 1.470(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.394(3) . ?
C10 C15 1.396(3) . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.390(2) . ?
C14 H14 0.9300 . ?
C16 C17 1.500(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.517(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O3 0.86 2.16 2.916(2) 146.1 1_565 yes
C7 H7A O3 0.96 2.64 3.530(3) 153.8 4 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 N2 C9 178.77(17) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C8 C1 C2 C3 -177.63(19) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C7 O1 C4 C3 2.0(3) . . . . ?
C7 O1 C4 C5 -177.77(19) . . . . ?
C2 C3 C4 O1 -179.59(19) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
O1 C4 C5 C6 -179.2(2) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
C8 C1 C6 C5 178.93(19) . . . . ?
N2 N1 C8 O3 1.5(3) . . . . ?
N2 N1 C8 C1 -178.50(15) . . . . ?
C2 C1 C8 O3 148.0(2) . . . . ?
C6 C1 C8 O3 -30.0(3) . . . . ?
C2 C1 C8 N1 -32.0(3) . . . . ?
C6 C1 C8 N1 150.05(19) . . . . ?
N1 N2 C9 C10 -173.95(16) . . . . ?
N2 C9 C10 C11 27.2(3) . . . . ?
N2 C9 C10 C15 -156.15(18) . . . . ?
C15 C10 C11 C12 -1.7(3) . . . . ?
C9 C10 C11 C12 175.02(18) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C14 1.9(3) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C16 O2 C15 C14 -0.1(2) . . . . ?
C16 O2 C15 C10 178.32(16) . . . . ?
C13 C14 C15 O2 176.74(18) . . . . ?
C13 C14 C15 C10 -1.6(3) . . . . ?
C11 C10 C15 O2 -175.66(16) . . . . ?
C9 C10 C15 O2 7.6(2) . . . . ?
C11 C10 C15 C14 2.8(3) . . . . ?
C9 C10 C15 C14 -173.97(17) . . . . ?
C15 O2 C16 C17 -177.55(15) . . . . ?
O2 C16 C17 C18 178.08(17) . . . . ?
