#------------------------------------------------------------------------------
#$Date: 2022-03-21 10:58:38 +0200 (Mon, 21 Mar 2022) $
#$Revision: 273864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/48/8104816.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_8104816
loop_
_publ_author_name
'Xi-Shi, Tai'
'Zhen, Ren'
'Li-Li, Liu'
'Ai-Ling, Zhang'
'Li-Hua, Wang'
_publ_section_title
;
 The crystal structure of
 (E)-2-(2-((2-picolinoylhydrazono)methyl)phenoxy)acetic acid dihydrate,
 C15H17N3O6
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              315
_journal_page_last               316
_journal_paper_doi               10.1515/ncrs-2020-0534
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C15 H13 N3 O4, 2(H2 O)'
_chemical_formula_sum            'C15 H17 N3 O6'
_chemical_formula_weight         335.32
_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   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                107.910(7)
_cell_angle_beta                 97.087(8)
_cell_angle_gamma                100.409(7)
_cell_formula_units_Z            2
_cell_length_a                   7.2155(8)
_cell_length_b                   10.7519(8)
_cell_length_c                   10.8562(8)
_cell_measurement_reflns_used    1935
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      27.1250
_cell_measurement_theta_min      3.1750
_cell_volume                     773.68(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     -8.00  86.00   1.00    4.50    --   11.90  37.00  90.00   94
  2  ω    -16.00  23.00   1.00    4.50    --  -11.27 -99.00  90.00   39
  3  ω     10.00  74.00   1.00    4.50    --   11.90-136.00 -76.00   64
  4  ω    -64.00  40.00   1.00    4.50    --   11.90 -19.00 -90.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0529137000
_diffrn_orient_matrix_UB_12      -0.0055400000
_diffrn_orient_matrix_UB_13      0.0497221000
_diffrn_orient_matrix_UB_21      -0.0805181000
_diffrn_orient_matrix_UB_22      -0.0409736000
_diffrn_orient_matrix_UB_23      -0.0491964000
_diffrn_orient_matrix_UB_31      0.0329454000
_diffrn_orient_matrix_UB_32      -0.0580447000
_diffrn_orient_matrix_UB_33      0.0009602000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0735
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5320
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.008
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2732
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0500
_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)+(0.0438P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1238
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1836
_reflns_number_total             2732
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0534_suppl.cif
_cod_data_source_block           w08
_cod_original_cell_volume        773.69(12)
_cod_database_code               8104816
_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.
;
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B), O6(H6A,H6B)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4A), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11),
 C12(H12)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
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
O1 O 0.6069(3) 0.83791(15) 0.51295(15) 0.0343(5) Uani 1 1 d . . . . .
O2 O 0.8323(2) 0.24274(14) 0.43498(14) 0.0276(4) Uani 1 1 d . . . . .
O3 O 0.8027(3) 0.11628(15) 0.18016(15) 0.0361(5) Uani 1 1 d . . . . .
O4 O 0.9119(3) -0.05242(15) 0.21748(15) 0.0328(5) Uani 1 1 d . . . . .
H4 H 0.895523 -0.082009 0.136762 0.049 Uiso 1 1 calc R U . . .
N1 N 0.5153(3) 0.65522(18) 0.17074(18) 0.0302(5) Uani 1 1 d . . . . .
N2 N 0.6282(3) 0.62735(17) 0.39873(17) 0.0235(5) Uani 1 1 d . . . . .
H2 H 0.606517 0.565728 0.322661 0.028 Uiso 1 1 calc R U . . .
N3 N 0.7051(3) 0.60268(18) 0.50855(17) 0.0231(5) Uani 1 1 d . . . . .
C1 C 0.5115(3) 0.7574(2) 0.2787(2) 0.0249(6) Uani 1 1 d . . . . .
C2 C 0.4448(4) 0.8691(2) 0.2737(2) 0.0296(6) Uani 1 1 d . . . . .
H2A H 0.444782 0.937979 0.350667 0.036 Uiso 1 1 calc R U . . .
C3 C 0.3783(4) 0.8755(2) 0.1516(3) 0.0345(7) Uani 1 1 d . . . . .
H3 H 0.331582 0.948689 0.144631 0.041 Uiso 1 1 calc R U . . .
C4 C 0.3822(4) 0.7720(3) 0.0404(3) 0.0379(7) Uani 1 1 d . . . . .
H4A H 0.339004 0.774163 -0.043100 0.046 Uiso 1 1 calc R U . . .
C5 C 0.4511(4) 0.6653(3) 0.0550(2) 0.0371(7) Uani 1 1 d . . . . .
H5 H 0.452859 0.595767 -0.020840 0.044 Uiso 1 1 calc R U . . .
C6 C 0.5864(3) 0.7461(2) 0.4083(2) 0.0246(6) Uani 1 1 d . . . . .
C7 C 0.7509(3) 0.4901(2) 0.4857(2) 0.0226(6) Uani 1 1 d . . . . .
H7 H 0.729395 0.432038 0.399153 0.027 Uiso 1 1 calc R U . . .
C8 C 0.8361(3) 0.4496(2) 0.5918(2) 0.0221(5) Uani 1 1 d . . . . .
C9 C 0.8820(4) 0.5367(2) 0.7218(2) 0.0281(6) Uani 1 1 d . . . . .
H9 H 0.855793 0.621496 0.741377 0.034 Uiso 1 1 calc R U . . .
C10 C 0.9652(4) 0.4996(2) 0.8219(2) 0.0318(6) Uani 1 1 d . . . . .
H10 H 0.995637 0.559081 0.908166 0.038 Uiso 1 1 calc R U . . .
C11 C 1.0035(4) 0.3734(2) 0.7935(2) 0.0294(6) Uani 1 1 d . . . . .
H11 H 1.059675 0.348053 0.861000 0.035 Uiso 1 1 calc R U . . .
C12 C 0.9590(4) 0.2849(2) 0.6659(2) 0.0262(6) Uani 1 1 d . . . . .
H12 H 0.984294 0.199923 0.647599 0.031 Uiso 1 1 calc R U . . .
C13 C 0.8768(3) 0.3223(2) 0.5652(2) 0.0215(5) Uani 1 1 d . . . . .
C14 C 0.8914(4) 0.1193(2) 0.4014(2) 0.0267(6) Uani 1 1 d . . . . .
H14A H 0.816243 0.057163 0.434923 0.032 Uiso 1 1 calc R U . . .
H14B H 1.025664 0.134507 0.439776 0.032 Uiso 1 1 calc R U . . .
C15 C 0.8618(4) 0.0624(2) 0.2544(2) 0.0247(6) Uani 1 1 d . . . . .
O5 O 0.8818(3) -0.1644(2) -0.03305(16) 0.0407(5) Uani 1 1 d G . . . .
H5A H 0.979458 -0.145209 -0.065953 0.061 Uiso 1 1 d G U . . .
H5B H 0.780487 -0.180286 -0.089671 0.061 Uiso 1 1 d G U . . .
O6 O 0.5732(3) -0.2216(2) -0.23826(17) 0.0445(5) Uani 1 1 d G . . . .
H6A H 0.472136 -0.191659 -0.233432 0.067 Uiso 1 1 d G U . . .
H6B H 0.607254 -0.223954 -0.310932 0.067 Uiso 1 1 d G 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
C13 O2 C14 117.20(16) . .
C15 O4 H4 109.5 . .
C5 N1 C1 116.62(19) . .
N3 N2 H2 119.5 . .
C6 N2 H2 119.5 . .
C6 N2 N3 120.97(17) . .
C7 N3 N2 115.02(18) . .
N1 C1 C2 123.4(2) . .
N1 C1 C6 116.28(18) . .
C2 C1 C6 120.3(2) . .
C1 C2 H2A 120.9 . .
C3 C2 C1 118.2(2) . .
C3 C2 H2A 120.9 . .
C2 C3 H3 120.5 . .
C4 C3 C2 119.0(2) . .
C4 C3 H3 120.5 . .
C3 C4 H4A 120.7 . .
C5 C4 C3 118.7(2) . .
C5 C4 H4A 120.7 . .
N1 C5 C4 124.1(2) . .
N1 C5 H5 117.9 . .
C4 C5 H5 117.9 . .
O1 C6 N2 123.9(2) . .
O1 C6 C1 122.38(19) . .
N2 C6 C1 113.74(19) . .
N3 C7 H7 119.2 . .
N3 C7 C8 121.7(2) . .
C8 C7 H7 119.2 . .
C9 C8 C7 121.06(19) . .
C9 C8 C13 118.2(2) . .
C13 C8 C7 120.75(19) . .
C8 C9 H9 119.4 . .
C10 C9 C8 121.2(2) . .
C10 C9 H9 119.4 . .
C9 C10 H10 120.2 . .
C9 C10 C11 119.7(2) . .
C11 C10 H10 120.2 . .
C10 C11 H11 119.8 . .
C12 C11 C10 120.4(2) . .
C12 C11 H11 119.8 . .
C11 C12 H12 120.0 . .
C11 C12 C13 120.0(2) . .
C13 C12 H12 120.0 . .
O2 C13 C8 115.26(18) . .
O2 C13 C12 124.20(18) . .
C12 C13 C8 120.5(2) . .
O2 C14 H14A 110.1 . .
O2 C14 H14B 110.1 . .
O2 C14 C15 107.93(17) . .
H14A C14 H14B 108.4 . .
C15 C14 H14A 110.1 . .
C15 C14 H14B 110.1 . .
O3 C15 O4 124.7(2) . .
O3 C15 C14 124.61(19) . .
O4 C15 C14 110.68(18) . .
H5A O5 H5B 109.5 . .
H6A O6 H6B 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C6 1.226(3) .
O2 C13 1.371(3) .
O2 C14 1.422(2) .
O3 C15 1.208(2) .
O4 H4 0.8200 .
O4 C15 1.307(2) .
N1 C1 1.344(3) .
N1 C5 1.328(3) .
N2 H2 0.8600 .
N2 N3 1.373(2) .
N2 C6 1.341(2) .
N3 C7 1.272(2) .
C1 C2 1.386(3) .
C1 C6 1.493(3) .
C2 H2A 0.9300 .
C2 C3 1.380(3) .
C3 H3 0.9300 .
C3 C4 1.375(3) .
C4 H4A 0.9300 .
C4 C5 1.374(3) .
C5 H5 0.9300 .
C7 H7 0.9300 .
C7 C8 1.457(3) .
C8 C9 1.392(3) .
C8 C13 1.402(3) .
C9 H9 0.9300 .
C9 C10 1.376(3) .
C10 H10 0.9300 .
C10 C11 1.383(3) .
C11 H11 0.9300 .
C11 C12 1.377(3) .
C12 H12 0.9300 .
C12 C13 1.381(3) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C14 C15 1.494(3) .
O5 H5A 0.8495 .
O5 H5B 0.8488 .
O6 H6A 0.8493 .
O6 H6B 0.8493 .
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
O2 C14 C15 O3 1.9(4) . . . .
O2 C14 C15 O4 -179.3(2) . . . .
N1 C1 C2 C3 0.2(4) . . . .
N1 C1 C6 O1 173.1(2) . . . .
N1 C1 C6 N2 -6.9(3) . . . .
N2 N3 C7 C8 179.3(2) . . . .
N3 N2 C6 O1 -2.4(4) . . . .
N3 N2 C6 C1 177.6(2) . . . .
N3 C7 C8 C9 -4.1(4) . . . .
N3 C7 C8 C13 176.8(2) . . . .
C1 N1 C5 C4 -0.2(4) . . . .
C1 C2 C3 C4 -0.5(4) . . . .
C2 C1 C6 O1 -6.2(4) . . . .
C2 C1 C6 N2 173.8(2) . . . .
C2 C3 C4 C5 0.4(4) . . . .
C3 C4 C5 N1 -0.1(5) . . . .
C5 N1 C1 C2 0.1(4) . . . .
C5 N1 C1 C6 -179.2(2) . . . .
C6 N2 N3 C7 -175.3(2) . . . .
C6 C1 C2 C3 179.5(2) . . . .
C7 C8 C9 C10 -179.0(2) . . . .
C7 C8 C13 O2 0.5(3) . . . .
C7 C8 C13 C12 179.5(2) . . . .
C8 C9 C10 C11 -0.4(4) . . . .
C9 C8 C13 O2 -178.6(2) . . . .
C9 C8 C13 C12 0.4(4) . . . .
C9 C10 C11 C12 0.1(4) . . . .
C10 C11 C12 C13 0.4(4) . . . .
C11 C12 C13 O2 178.2(2) . . . .
C11 C12 C13 C8 -0.7(4) . . . .
C13 O2 C14 C15 -169.5(2) . . . .
C13 C8 C9 C10 0.1(4) . . . .
C14 O2 C13 C8 172.8(2) . . . .
C14 O2 C13 C12 -6.1(3) . . . .
