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#$Date: 2022-06-03 10:10:38 +0300 (Fri, 03 Jun 2022) $
#$Revision: 275758 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/53/8105327.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.
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data_8105327
loop_
_publ_author_name
'Mossine, Valeri V.'
'Kelley, Steven P.'
'Mawhinney, Thomas P.'
_publ_section_title
;
 Crystal structure of
 (E)-3-methoxy-N′-(1-(pyridin-2-yl)ethylidene)benzohydrazide,
 C15H15N3O2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              907
_journal_page_last               909
_journal_paper_doi               10.1515/ncrs-2020-0097
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C15 H15 N3 O2'
_chemical_formula_sum            'C15 H15 N3 O2'
_chemical_formula_weight         269.30
_chemical_name_common            '2-acetylpyridine m-anisoyl hydrazone'
_chemical_name_systematic
(E)-3-methoxy-N'-(1-(pyridin-2-yl)ethylidene)benzohydrazide
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9831(2)
_cell_length_b                   10.6486(3)
_cell_length_c                   15.7222(4)
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.52
_cell_measurement_theta_min      2.59
_cell_volume                     1336.53(6)
_computing_cell_refinement       'Bruker Apex3 and SAINT [1]'
_computing_data_collection       'Bruker Apex3 and SAINT [1]'
_computing_data_reduction        'Bruker Apex3 and SAINT [1]'
_computing_molecular_graphics    'CrystalExplorer 17.5 [5], Mercury [6]'
_computing_publication_material  'Olex2 [4]'
_computing_structure_refinement  'SHELXL [3]'
_computing_structure_solution    'SHELXS [2]'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            34842
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.675
_diffrn_reflns_theta_min         2.591
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       Prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1493 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3790
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0340
_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)+(0.0430P)²+0.2468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0799
_reflns_Friedel_coverage         0.930
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3385
_reflns_number_total             3790
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0097_suppl.cif
_cod_data_source_block           s1_a
_cod_database_code               8105327
_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_max   0.992
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C3(H3), C11(H11), C5(H5), C14(H14), C13(H13), C12(H12)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C15(H15A,H15B,H15C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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 0.65856(15) 0.64702(11) 0.53292(9) 0.0163(3) Uani 1 1 d . . . . .
O2 O 1.13033(16) 0.94314(11) 0.64302(8) 0.0172(3) Uani 1 1 d . . . . .
N1 N 0.81973(18) 0.47369(13) 0.50812(9) 0.0123(3) Uani 1 1 d . . . . .
N2 N 0.69467(17) 0.42449(13) 0.45744(9) 0.0122(3) Uani 1 1 d . . . . .
N3 N 0.5631(2) 0.13527(14) 0.37099(10) 0.0164(3) Uani 1 1 d . . . . .
C1 C 0.7893(2) 0.58803(16) 0.54361(10) 0.0115(3) Uani 1 1 d . . . . .
C2 C 0.9256(2) 0.63898(15) 0.59947(11) 0.0114(3) Uani 1 1 d . . . . .
C3 C 0.9580(2) 0.76818(15) 0.59386(11) 0.0120(3) Uani 1 1 d . . . . .
C4 C 1.0831(2) 0.81951(16) 0.64451(11) 0.0132(3) Uani 1 1 d . . . . .
C5 C 1.1709(2) 0.74460(17) 0.70209(11) 0.0156(3) Uani 1 1 d . . . . .
C6 C 1.1347(2) 0.61830(17) 0.70823(12) 0.0157(3) Uani 1 1 d . . . . .
C7 C 1.0126(2) 0.56340(15) 0.65637(10) 0.0134(3) Uani 1 1 d . . . . .
C8 C 1.0461(2) 1.02502(16) 0.58479(12) 0.0190(4) Uani 1 1 d . . . . .
C9 C 0.7113(2) 0.31023(15) 0.43228(11) 0.0123(3) Uani 1 1 d . . . . .
C10 C 0.5685(2) 0.26067(16) 0.38103(10) 0.0125(3) Uani 1 1 d . . . . .
C11 C 0.4476(2) 0.34046(17) 0.34663(11) 0.0169(4) Uani 1 1 d . . . . .
C12 C 0.3153(3) 0.28838(19) 0.30172(13) 0.0231(4) Uani 1 1 d . . . . .
C13 C 0.3086(3) 0.15935(19) 0.29134(14) 0.0233(4) Uani 1 1 d . . . . .
C14 C 0.4345(3) 0.08763(17) 0.32668(13) 0.0198(4) Uani 1 1 d . . . . .
C15 C 0.8537(2) 0.22489(17) 0.45435(14) 0.0225(4) Uani 1 1 d . . . . .
H1 H 0.916(3) 0.438(2) 0.5112(14) 0.015 Uiso 1 1 d R . . . .
H3 H 0.895440 0.819679 0.556100 0.014 Uiso 1 1 calc R . . . .
H5 H 1.255451 0.780516 0.736965 0.019 Uiso 1 1 calc R . . . .
H6 H 1.193383 0.567925 0.748208 0.019 Uiso 1 1 calc R . . . .
H7 H 0.989501 0.476039 0.660006 0.016 Uiso 1 1 calc R . . . .
H8A H 1.093279 1.109719 0.589322 0.029 Uiso 1 1 calc GR . . . .
H8B H 0.926414 1.027556 0.598559 0.029 Uiso 1 1 calc GR . . . .
H8C H 1.060933 0.993830 0.526631 0.029 Uiso 1 1 calc GR . . . .
H11 H 0.455732 0.428818 0.353844 0.020 Uiso 1 1 calc R . . . .
H12 H 0.230380 0.340505 0.278372 0.028 Uiso 1 1 calc R . . . .
H13 H 0.219625 0.121204 0.260656 0.028 Uiso 1 1 calc R . . . .
H14 H 0.429805 -0.000820 0.319174 0.024 Uiso 1 1 calc R . . . .
H15A H 0.877896 0.231453 0.515294 0.034 Uiso 1 1 calc GR . . . .
H15B H 0.953112 0.249219 0.421713 0.034 Uiso 1 1 calc GR . . . .
H15C H 0.823311 0.138099 0.440495 0.034 Uiso 1 1 calc GR . . . .
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
C4 O2 C8 117.83(13) . .
N2 N1 H1 120.9(14) . .
C1 N1 N2 116.54(13) . .
C1 N1 H1 122.0(14) . .
C9 N2 N1 117.50(14) . .
C14 N3 C10 117.45(16) . .
O1 C1 N1 123.55(15) . .
O1 C1 C2 120.74(15) . .
N1 C1 C2 115.70(14) . .
C7 C2 C1 122.01(15) . .
C7 C2 C3 121.12(15) . .
C3 C2 C1 116.84(15) . .
C4 C3 C2 118.83(15) . .
C4 C3 H3 120.6 . .
C2 C3 H3 120.6 . .
O2 C4 C3 124.50(15) . .
O2 C4 C5 114.97(15) . .
C3 C4 C5 120.54(15) . .
C4 C5 H5 120.1 . .
C6 C5 C4 119.83(16) . .
C6 C5 H5 120.1 . .
C7 C6 H6 119.6 . .
C5 C6 H6 119.6 . .
C5 C6 C7 120.86(16) . .
C2 C7 C6 118.77(15) . .
C2 C7 H7 120.6 . .
C6 C7 H7 120.6 . .
O2 C8 H8A 109.5 . .
O2 C8 H8B 109.5 . .
O2 C8 H8C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N2 C9 C10 114.93(15) . .
N2 C9 C15 125.57(16) . .
C10 C9 C15 119.40(15) . .
N3 C10 C9 116.01(15) . .
N3 C10 C11 122.48(15) . .
C11 C10 C9 121.51(15) . .
C10 C11 H11 120.6 . .
C12 C11 C10 118.75(16) . .
C12 C11 H11 120.6 . .
C11 C12 H12 120.4 . .
C13 C12 C11 119.10(18) . .
C13 C12 H12 120.4 . .
C14 C13 H13 120.9 . .
C14 C13 C12 118.29(17) . .
C12 C13 H13 120.9 . .
N3 C14 H14 118.0 . .
N3 C14 C13 123.92(17) . .
C13 C14 H14 118.0 . .
C9 C15 H15A 109.5 . .
C9 C15 H15B 109.5 . .
C9 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.229(2) .
O2 C4 1.370(2) .
O2 C8 1.432(2) .
N1 H1 0.86(2) .
N1 C1 1.361(2) .
N2 N1 1.3806(18) .
N2 C9 1.286(2) .
N3 C10 1.345(2) .
N3 C14 1.340(2) .
C1 C2 1.500(2) .
C2 C7 1.389(2) .
C2 C3 1.403(2) .
C3 H3 0.9500 .
C4 C3 1.389(2) .
C4 C5 1.396(2) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C6 C7 1.399(2) .
C6 C5 1.379(2) .
C7 H7 0.9500 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C15 1.496(2) .
C10 C9 1.493(2) .
C10 C11 1.395(2) .
C11 H11 0.9500 .
C11 C12 1.386(3) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C13 C12 1.385(3) .
C14 H14 0.9500 .
C14 C13 1.379(3) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
