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#$Date: 2022-05-09 10:49:23 +0300 (Mon, 09 May 2022) $
#$Revision: 275262 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/51/8105175.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_8105175
loop_
_publ_author_name
'Mossine, Valeri V.'
'Kelley, Steven P.'
'Mawhinney, Thomas P.'
_publ_section_title
;
 Crystal structure of
 (E)-N′-(1-(2-hydroxy-4-methoxyphenyl)ethylidene)
 isonicotinohydrazide, C15H15N3O3
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              195
_journal_page_last               197
_journal_paper_doi               10.1515/ncrs-2021-0435
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C15 H15 N3 O3'
_chemical_formula_sum            'C15 H15 N3 O3'
_chemical_formula_weight         285.30
_chemical_name_systematic
; 
(E)-N'-(1-(2-hydroxy-4-methoxyphenyl)ethylidene)\
isonicotinohydrazide
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                112.7059(8)
_cell_angle_beta                 92.4309(8)
_cell_angle_gamma                115.2776(7)
_cell_formula_units_Z            2
_cell_length_a                   9.0752(2)
_cell_length_b                   9.1969(2)
_cell_length_c                   9.9519(2)
_cell_measurement_reflns_used    9851
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      46.96
_cell_measurement_theta_min      2.29
_cell_volume                     671.16(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'shutterless omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            114957
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         47.014
_diffrn_reflns_theta_min         2.290
_diffrn_source                   'Sealed Source Mo with TRIUMPH optics'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.3578
_exptl_absorpt_correction_T_min  0.3070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.696
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         12029
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0646P)²+0.0559P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1113
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10312
_reflns_number_total             12029
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0435_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105175
_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   0.988
_shelx_estimated_absorpt_t_min   0.961
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H) groups
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 1.38839(5) 1.54660(5) 1.23512(4) 0.01559(5) Uani 1 1 d . . . . .
H1 H 1.4238(11) 1.5677(11) 1.3357(9) 0.019 Uiso 1 1 d R . . . .
C2 C 1.26066(4) 1.37850(5) 1.13136(4) 0.01430(5) Uani 1 1 d . . . . .
H2B H 1.2052(11) 1.2847(11) 1.1577(9) 0.017 Uiso 1 1 d R . . . .
C3 C 1.22084(4) 1.34826(4) 0.98295(4) 0.01247(5) Uani 1 1 d . . . . .
C4 C 1.30377(4) 1.48893(5) 0.94615(4) 0.01365(5) Uani 1 1 d . . . . .
H4 H 1.2761(10) 1.4733(11) 0.8422(9) 0.016 Uiso 1 1 d R . . . .
C5 C 1.42654(4) 1.65340(5) 1.05875(4) 0.01459(5) Uani 1 1 d . . . . .
H5 H 1.4898(10) 1.7537(11) 1.0363(9) 0.018 Uiso 1 1 d R . . . .
C6 C 1.09154(4) 1.16559(5) 0.86686(4) 0.01488(5) Uani 1 1 d . . . . .
C7 C 1.07521(4) 0.83347(4) 0.52745(4) 0.01247(5) Uani 1 1 d . . . . .
C8 C 1.24427(5) 0.90730(6) 0.49466(5) 0.02019(7) Uani 1 1 d . . . . .
H8A H 1.3179(13) 0.8866(13) 0.5385(11) 0.030 Uiso 1 1 d R . . . .
H8B H 1.2969(13) 1.0355(13) 0.5292(11) 0.030 Uiso 1 1 d R . . . .
H8C H 1.2340(13) 0.8617(13) 0.3902(11) 0.030 Uiso 1 1 d R . . . .
C9 C 0.94432(4) 0.64664(4) 0.43348(3) 0.01144(4) Uani 1 1 d . . . . .
C10 C 0.77924(4) 0.58063(4) 0.45476(3) 0.01172(4) Uani 1 1 d . . . . .
C11 C 0.65747(4) 0.40107(4) 0.36802(4) 0.01260(5) Uani 1 1 d . . . . .
H11 H 0.5439(10) 0.3652(11) 0.3897(9) 0.015 Uiso 1 1 d R . . . .
C12 C 0.69869(4) 0.28329(4) 0.26127(4) 0.01195(4) Uani 1 1 d . . . . .
C13 C 0.86150(4) 0.34382(4) 0.23877(4) 0.01354(5) Uani 1 1 d . . . . .
H13 H 0.8881(10) 0.2575(11) 0.1633(9) 0.016 Uiso 1 1 d R . . . .
C14 C 0.97989(4) 0.52271(5) 0.32373(4) 0.01319(5) Uani 1 1 d . . . . .
H14 H 1.0893(10) 0.5636(11) 0.3046(9) 0.016 Uiso 1 1 d R . . . .
C15 C 0.41500(5) 0.05115(5) 0.17986(5) 0.01735(6) Uani 1 1 d . . . . .
H15A H 0.3526(12) -0.0773(13) 0.1030(10) 0.026 Uiso 1 1 d R . . . .
H15B H 0.3797(12) 0.1246(13) 0.1581(10) 0.026 Uiso 1 1 d R . . . .
H15C H 0.4027(12) 0.0560(12) 0.2809(10) 0.026 Uiso 1 1 d R . . . .
N1 N 1.47189(4) 1.68281(4) 1.20065(4) 0.01568(5) Uani 1 1 d . . . . .
N2 N 1.14458(4) 1.09676(4) 0.74218(3) 0.01441(5) Uani 1 1 d . . . . .
H2A H 1.2524(12) 1.1488(12) 0.7429(10) 0.024 Uiso 1 1 d R . . . .
N3 N 1.03301(4) 0.92441(4) 0.63899(3) 0.01403(4) Uani 1 1 d . . . . .
O1 O 0.95204(4) 1.08579(5) 0.88383(4) 0.02588(7) Uani 1 1 d . . . . .
O2 O 0.72951(4) 0.68512(4) 0.55778(3) 0.01644(5) Uani 1 1 d . . . . .
H2 H 0.8266(13) 0.7914(13) 0.6122(11) 0.030 Uiso 1 1 d R . . . .
O3 O 0.58672(3) 0.10699(4) 0.17321(3) 0.01561(5) Uani 1 1 d . . . . .
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
C12 O3 C15 116.52(3) . .
C12 C11 C10 119.97(3) . .
C11 C10 C9 121.01(3) . .
O2 C10 C11 116.15(3) . .
O2 C10 C9 122.84(3) . .
C10 C9 C7 121.56(3) . .
C14 C9 C10 116.96(3) . .
C14 C9 C7 121.39(3) . .
C7 N3 N2 121.81(3) . .
O3 C12 C11 123.11(3) . .
O3 C12 C13 116.47(3) . .
C11 C12 C13 120.42(3) . .
C9 C7 C8 121.20(3) . .
N3 C7 C9 114.84(3) . .
N3 C7 C8 123.95(3) . .
C6 N2 N3 115.23(3) . .
C14 C13 C12 118.92(3) . .
C4 C3 C2 118.97(3) . .
C4 C3 C6 121.53(3) . .
C2 C3 C6 119.50(3) . .
C13 C14 C9 122.70(3) . .
C5 N1 C1 117.37(3) . .
C5 C4 C3 118.41(3) . .
C1 C2 C3 118.23(3) . .
N1 C5 C4 123.48(3) . .
N2 C6 C3 114.06(3) . .
O1 C6 N2 123.63(3) . .
O1 C6 C3 122.31(3) . .
N1 C1 C2 123.43(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 C12 1.3602(4) .
O3 C15 1.4312(5) .
C11 C10 1.3977(4) .
C11 C12 1.3904(4) .
C10 C9 1.4168(4) .
C10 O2 1.3517(4) .
C9 C7 1.4698(4) .
C9 C14 1.4068(4) .
N3 C7 1.2928(4) .
N3 N2 1.3700(4) .
C12 C13 1.4018(5) .
C7 C8 1.4984(5) .
N2 C6 1.3699(5) .
C13 C14 1.3840(5) .
C3 C4 1.3900(5) .
C3 C2 1.3932(5) .
C3 C6 1.4957(5) .
N1 C5 1.3407(5) .
N1 C1 1.3432(5) .
C4 C5 1.3897(5) .
C2 C1 1.3913(5) .
C6 O1 1.2208(5) .
