#------------------------------------------------------------------------------
#$Date: 2025-08-23 02:36:08 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/20/8102005.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_8102005
loop_
_publ_author_name
'Tai, X.-S.'
'Kong, F.-Y.'
_publ_section_title
;Crystal structure of 2'-hydroxyacetophenone nicotinoyl-hydrazone monohydrate,
 C₁₄H₁₅N₃O₃ · H₂O
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              341
_journal_page_last               342
_journal_volume                  221
_journal_year                    2006
_chemical_formula_structural     'C14H15N3O3 &#x00B7; H2O'
_chemical_formula_sum            'C14 H15 N3 O3'
_chemical_formula_weight         273.29
_chemical_name_systematic
; 
2'-hydroxyacetophenone nicotinoylhydrazone monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                81.28(3)
_cell_angle_beta                 86.26(3)
_cell_angle_gamma                70.48(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6795(17)
_cell_length_b                   8.8771(18)
_cell_length_c                   9.2728(19)
_cell_measurement_reflns_used    389
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      2
_cell_volume                     665.5(3)
_computing_cell_refinement       raxis
_computing_data_collection       raxis
_computing_data_reduction        raxis
_computing_molecular_graphics    texsan
_computing_publication_material  texsan
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.828
_diffrn_measured_fraction_theta_max 0.828
_diffrn_measurement_device_type  'Rigaku R-AXIS IV'
_diffrn_measurement_method       omega
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            1937
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9835
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.046(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         1937
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0642
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1027P)²+0.1228P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1625
_refine_ls_wR_factor_ref         0.1769
_reflns_number_gt                1420
_reflns_number_total             1937
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1820.cff
_cod_data_source_block           p-1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        665.5(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8102005
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5665(3) 0.7665(3) 0.5528(3) 0.0514(7) Uani 1 2 i d . . .
N2 N 0.5104(3) 0.7310(3) 0.4293(3) 0.0526(7) Uani 1 2 i d . . .
H2E H 0.582(4) 0.687(4) 0.359(3) 0.059(9) Uiso 1 2 i d . . .
N3 N 0.1055(3) 0.5624(3) 0.2302(3) 0.0609(7) Uani 1 2 i d . . .
O1 O 0.5124(3) 0.8071(4) 0.8202(3) 0.0764(8) Uani 1 2 i d . . .
O2 O 0.2787(3) 0.7294(3) 0.5547(2) 0.0650(7) Uani 1 2 i d . . .
O3 O 0.2203(3) 0.4627(3) -0.2600(3) 0.0659(7) Uiso 1 2 i d . . .
C1 C 0.6527(4) 0.8427(4) 0.8082(3) 0.0558(8) Uani 1 2 i d . . .
C2 C 0.7122(5) 0.8682(5) 0.9352(4) 0.0720(10) Uani 1 2 i d . . .
H2A H 0.6527 0.8647 1.0220 0.086 Uiso 1 2 i calc R . .
C3 C 0.8565(5) 0.8985(5) 0.9341(4) 0.0771(11) Uani 1 2 i d . . .
H3A H 0.8943 0.9153 1.0198 0.093 Uiso 1 2 i calc R . .
C4 C 0.9457(5) 0.9040(5) 0.8071(4) 0.0759(11) Uani 1 2 i d . . .
H4A H 1.0451 0.9225 0.8071 0.091 Uiso 1 2 i calc R . .
C5 C 0.8885(4) 0.8823(4) 0.6799(4) 0.0619(9) Uani 1 2 i d . . .
H5A H 0.9496 0.8875 0.5942 0.074 Uiso 1 2 i calc R . .
C6 C 0.7401(4) 0.8527(3) 0.6763(3) 0.0492(7) Uani 1 2 i d . . .
C7 C 0.6832(3) 0.8257(3) 0.5385(3) 0.0473(7) Uani 1 2 i d . . .
C8 C 0.7591(4) 0.8705(4) 0.3961(3) 0.0604(9) Uani 1 2 i d . . .
H8A H 0.7081 0.8459 0.3180 0.091 Uiso 1 2 i calc R . .
H8B H 0.8739 0.8103 0.3962 0.091 Uiso 1 2 i calc R . .
H8C H 0.7440 0.9838 0.3827 0.091 Uiso 1 2 i calc R . .
C9 C 0.3643(4) 0.7061(3) 0.4437(3) 0.0513(8) Uani 1 2 i d . . .
C10 C 0.1737(4) 0.6034(4) 0.3358(3) 0.0559(8) Uani 1 2 i d . . .
H10A H 0.1292 0.5952 0.4295 0.067 Uiso 1 2 i calc R . .
C11 C 0.3078(3) 0.6578(3) 0.3148(3) 0.0495(7) Uani 1 2 i d . . .
C12 C 0.3732(4) 0.6682(4) 0.1751(4) 0.0639(9) Uani 1 2 i d . . .
H12A H 0.4624 0.7043 0.1553 0.077 Uiso 1 2 i calc R . .
C13 C 0.3045(4) 0.6245(5) 0.0664(4) 0.0699(10) Uani 1 2 i d . . .
H13A H 0.3470 0.6302 -0.0281 0.084 Uiso 1 2 i calc R . .
C14 C 0.1732(4) 0.5724(4) 0.0976(4) 0.0634(9) Uani 1 2 i d . . .
H14A H 0.1288 0.5425 0.0224 0.076 Uiso 1 2 i calc R . .
H1E H 0.501(5) 0.782(5) 0.729(5) 0.112(16) Uiso 1 2 i d . . .
H3F H 0.088(8) 0.472(8) -0.257(6) 0.19(2) Uiso 1 2 i d . . .
H3E H 0.200(5) 0.555(5) -0.306(4) 0.085(12) Uiso 1 2 i 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
_geom_angle_publ_flag
C7 N1 N2 118.8(3) . . ?
C9 N2 N1 116.1(2) . . ?
C9 N2 H2E 119.1(19) . . ?
N1 N2 H2E 120.2(19) . . ?
C10 N3 C14 116.8(3) . . ?
C1 O1 H1E 104(3) . . ?
H3F O3 H3E 92(4) . . ?
O1 C1 C2 117.2(3) . . ?
O1 C1 C6 123.4(3) . . ?
C2 C1 C6 119.5(3) . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H2A 119.5 . . ?
C1 C2 H2A 119.5 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C5 C6 C1 117.7(3) . . ?
C5 C6 C7 120.4(3) . . ?
C1 C6 C7 121.8(3) . . ?
N1 C7 C6 115.1(3) . . ?
N1 C7 C8 124.9(3) . . ?
C6 C7 C8 120.0(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 N2 121.8(3) . . ?
O2 C9 C11 121.6(3) . . ?
N2 C9 C11 116.5(3) . . ?
N3 C10 C11 124.0(3) . . ?
N3 C10 H10A 118.0 . . ?
C11 C10 H10A 118.0 . . ?
C12 C11 C10 117.2(3) . . ?
C12 C11 C9 125.6(3) . . ?
C10 C11 C9 117.1(3) . . ?
C13 C12 C11 118.9(3) . . ?
C13 C12 H12A 120.6 . . ?
C11 C12 H12A 120.6 . . ?
C14 C13 C12 119.7(3) . . ?
C14 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?
N3 C14 C13 123.3(3) . . ?
N3 C14 H14A 118.3 . . ?
C13 C14 H14A 118.3 . . ?
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
N1 C7 1.280(4) . ?
N1 N2 1.390(3) . ?
N2 C9 1.354(4) . ?
N2 H2E 0.91(3) . ?
N3 C10 1.331(4) . ?
N3 C14 1.331(4) . ?
O1 C1 1.350(4) . ?
O1 H1E 0.93(4) . ?
O2 C9 1.231(3) . ?
O3 H3F 1.12(7) . ?
O3 H3E 0.83(4) . ?
C1 C2 1.394(4) . ?
C1 C6 1.404(4) . ?
C2 C3 1.364(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.370(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.373(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.401(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.479(4) . ?
C7 C8 1.496(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C11 1.492(4) . ?
C10 C11 1.395(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.382(4) . ?
C12 C13 1.369(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.366(5) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
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
N2 H2E O3 0.91(3) 2.05(3) 2.922(4) 161(3) 2_665
O3 H3F N3 1.12(7) 1.80(7) 2.902(4) 166(5) 2_565
O3 H3E O2 0.83(4) 2.13(4) 2.876(4) 150(4) 1_554
O1 H1E N1 0.93(4) 1.70(5) 2.551(3) 150(4) .
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
C7 N1 N2 C9 -164.7(3) . . . . ?
O1 C1 C2 C3 177.4(3) . . . . ?
C6 C1 C2 C3 -1.8(5) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C2 C3 C4 C5 1.3(6) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
C4 C5 C6 C1 -1.2(5) . . . . ?
C4 C5 C6 C7 -178.5(3) . . . . ?
O1 C1 C6 C5 -176.7(3) . . . . ?
C2 C1 C6 C5 2.4(5) . . . . ?
O1 C1 C6 C7 0.5(5) . . . . ?
C2 C1 C6 C7 179.6(3) . . . . ?
N2 N1 C7 C6 -177.3(2) . . . . ?
N2 N1 C7 C8 4.1(4) . . . . ?
C5 C6 C7 N1 165.8(3) . . . . ?
C1 C6 C7 N1 -11.4(4) . . . . ?
C5 C6 C7 C8 -15.6(4) . . . . ?
C1 C6 C7 C8 167.3(3) . . . . ?
N1 N2 C9 O2 7.0(4) . . . . ?
N1 N2 C9 C11 -176.3(2) . . . . ?
C14 N3 C10 C11 1.2(5) . . . . ?
N3 C10 C11 C12 -0.4(5) . . . . ?
N3 C10 C11 C9 177.2(3) . . . . ?
O2 C9 C11 C12 162.7(3) . . . . ?
N2 C9 C11 C12 -14.0(5) . . . . ?
O2 C9 C11 C10 -14.7(4) . . . . ?
N2 C9 C11 C10 168.6(3) . . . . ?
C10 C11 C12 C13 -0.3(5) . . . . ?
C9 C11 C12 C13 -177.7(3) . . . . ?
C11 C12 C13 C14 0.3(5) . . . . ?
C10 N3 C14 C13 -1.2(5) . . . . ?
C12 C13 C14 N3 0.5(6) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653904
2 PubChem 139206878
