#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:28:18 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257835 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/98/7059805.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_7059805
loop_
_publ_author_name
'Topić, Edi'
'Landripet, Ivana'
'Duguin, Maëlle'
'Pisk, Jana'
'Đilović, Ivica'
'Vrdoljak, Višnja'
'Rubčić, Mirta'
_publ_section_title
;
 Coordinating and supramolecular prospects of unsymmetrically substituted
 carbohydrazides
;
_journal_issue                   31
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13357
_journal_page_last               13367
_journal_paper_doi               10.1039/D0NJ03106B
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C14 H13 N5 O2, H2 O'
_chemical_formula_sum            'C14 H15 N5 O3'
_chemical_formula_weight         301.31
_chemical_name_systematic
'3-[(E)-[(1-hydroxyphenyl-2-yl)methylidene]amino]-1-[(E)-[(pyridin-3-yl)methylidene]amino]urea hydrate'
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-27 deposited with the CCDC.	2020-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.079(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3767(6)
_cell_length_b                   7.7407(7)
_cell_length_c                   30.099(3)
_cell_measurement_reflns_used    1568
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.5910
_cell_measurement_theta_min      4.3960
_cell_volume                     1483.5(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   10.00   80.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4994    0.0000  150.0000 70

#__ type_ start__ end____ width___ exp.time_
  2 omega  -42.00  -12.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4994  -37.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
  3 omega   -4.00   22.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4994  -37.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   -2.00   88.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4994   19.0000    0.0000 90

#__ type_ start__ end____ width___ exp.time_
  5 omega    8.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4994   37.0000   60.0000 82

#__ type_ start__ end____ width___ exp.time_
  6 omega   45.00   84.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4994  179.0000   30.0000 39

#__ type_ start__ end____ width___ exp.time_
  7 omega   25.00   50.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4994   37.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega    4.00   30.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4994   19.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   42.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4994   19.0000 -150.0000 48

#__ type_ start__ end____ width___ exp.time_
 10 omega   49.00   84.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4994  179.0000 -150.0000 35

#__ type_ start__ end____ width___ exp.time_
 11 omega  -57.00  -32.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.6557  179.0000    0.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0401041000
_diffrn_orient_matrix_UB_12      -0.0197174000
_diffrn_orient_matrix_UB_13      0.0218507000
_diffrn_orient_matrix_UB_21      -0.0792139000
_diffrn_orient_matrix_UB_22      0.0519662000
_diffrn_orient_matrix_UB_23      0.0089033000
_diffrn_orient_matrix_UB_31      -0.0672946000
_diffrn_orient_matrix_UB_32      -0.0728347000
_diffrn_orient_matrix_UB_33      0.0004646000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_unetI/netI     0.1285
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            18491
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.839
_diffrn_reflns_theta_min         4.293
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         5029
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.2160
_refine_ls_R_factor_gt           0.0716
_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)+(0.0249P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1320
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1845
_reflns_number_total             5029
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj03106b2.cif
_cod_data_source_block           H2L3pysalxH2O
_cod_depositor_comments
;Adding full bibliography for 7059802--7059812.cif.

 Adding full bibliography for 7059802--7059812.cif.
;
_cod_database_code               7059805
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C16N5O2H8
_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   0.995
_shelx_estimated_absorpt_t_min   0.990
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 H3-N3
 0.86 with sigma of 0.02
 N2-H2
 0.86 with sigma of 0.02
 O1-H1
 0.82 with sigma of 0.02
 O3-H3C
 0.82 with sigma of 0.02
 O3-H3B
 0.82 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C7(H7), C11(H11), C14(H14), C6(H6), C13(H13), C12(H12), C3(H3A),
 C5(H5), C4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O2 O 0.9752(2) 0.11533(19) 0.44855(5) 0.0479(4) Uani 1 1 d . . . . .
N4 N 0.5774(2) 0.1861(2) 0.52272(6) 0.0408(4) Uani 1 1 d . . . . .
O3 O 1.2518(3) 0.4033(2) 0.44864(8) 0.0757(6) Uani 1 1 d D . . . .
O1 O 0.9856(3) 0.2875(3) 0.33363(6) 0.0709(6) Uani 1 1 d D . . . .
N3 N 0.7622(3) 0.1307(2) 0.50555(6) 0.0439(5) Uani 1 1 d D . . . .
N2 N 0.6624(3) 0.2568(2) 0.43810(6) 0.0450(5) Uani 1 1 d D . . . .
N1 N 0.7141(3) 0.2911(2) 0.39516(6) 0.0427(4) Uani 1 1 d . . . . .
N5 N 0.0324(3) 0.3322(2) 0.58613(8) 0.0597(6) Uani 1 1 d . . . . .
C8 C 0.8069(3) 0.1671(3) 0.46299(8) 0.0413(5) Uani 1 1 d . . . . .
C10 C 0.3687(3) 0.1912(3) 0.58637(7) 0.0412(5) Uani 1 1 d . . . . .
C1 C 0.6356(3) 0.4078(3) 0.32382(7) 0.0422(5) Uani 1 1 d . . . . .
C9 C 0.5546(3) 0.1429(3) 0.56325(8) 0.0434(6) Uani 1 1 d . . . . .
H9 H 0.659502 0.078953 0.578285 0.052 Uiso 1 1 calc R . . . .
C7 C 0.5804(3) 0.3659(3) 0.36857(7) 0.0439(5) Uani 1 1 d . . . . .
H7 H 0.447854 0.393509 0.377934 0.053 Uiso 1 1 calc R . . . .
C11 C 0.2075(3) 0.2899(3) 0.56613(8) 0.0497(6) Uani 1 1 d . . . . .
H11 H 0.222564 0.328318 0.537195 0.060 Uiso 1 1 calc R . . . .
C2 C 0.8340(3) 0.3705(3) 0.30837(8) 0.0502(6) Uani 1 1 d . . . . .
C14 C 0.3460(4) 0.1369(3) 0.62947(8) 0.0562(7) Uani 1 1 d . . . . .
H14 H 0.450887 0.071856 0.644168 0.067 Uiso 1 1 calc R . . . .
C6 C 0.4913(4) 0.4929(3) 0.29524(8) 0.0575(7) Uani 1 1 d . . . . .
H6 H 0.358167 0.517020 0.304835 0.069 Uiso 1 1 calc R . . . .
C13 C 0.1659(4) 0.1798(4) 0.65072(9) 0.0691(8) Uani 1 1 d . . . . .
H13 H 0.147207 0.144138 0.679742 0.083 Uiso 1 1 calc R . . . .
C12 C 0.0167(4) 0.2760(4) 0.62789(10) 0.0692(8) Uani 1 1 d . . . . .
H12 H -0.104038 0.304383 0.642303 0.083 Uiso 1 1 calc R . . . .
C3 C 0.8824(4) 0.4202(4) 0.26584(8) 0.0683(8) Uani 1 1 d . . . . .
H3A H 1.014070 0.395220 0.255623 0.082 Uiso 1 1 calc R . . . .
C5 C 0.5405(4) 0.5424(3) 0.25306(9) 0.0705(8) Uani 1 1 d . . . . .
H5 H 0.442210 0.599632 0.234464 0.085 Uiso 1 1 calc R . . . .
C4 C 0.7377(5) 0.5057(4) 0.23885(9) 0.0741(8) Uani 1 1 d . . . . .
H4 H 0.772704 0.539617 0.210545 0.089 Uiso 1 1 calc R . . . .
H3 H 0.849(3) 0.058(3) 0.5222(7) 0.089 Uiso 1 1 d DR . . . .
H2 H 0.541(3) 0.298(3) 0.4481(8) 0.089 Uiso 1 1 d DR . . . .
H1 H 0.933(4) 0.268(3) 0.3588(6) 0.089 Uiso 1 1 d DR . . . .
H3B H 1.172(4) 0.316(3) 0.4471(9) 0.089 Uiso 1 1 d DR . . . .
H3C H 1.182(4) 0.490(3) 0.4399(9) 0.089 Uiso 1 1 d DR . . . .
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
C9 N4 N3 114.75(18) . . ?
C8 N3 N4 121.08(18) . . ?
C8 N2 N1 115.45(17) . . ?
C7 N1 N2 119.38(17) . . ?
C11 N5 C12 116.7(2) . . ?
O2 C8 N3 119.4(2) . . ?
O2 C8 N2 123.2(2) . . ?
N2 C8 N3 117.33(19) . . ?
C11 C10 C9 122.1(2) . . ?
C14 C10 C9 120.1(2) . . ?
C14 C10 C11 117.8(2) . . ?
C2 C1 C7 122.1(2) . . ?
C6 C1 C7 119.7(2) . . ?
C6 C1 C2 118.1(2) . . ?
N4 C9 C10 121.7(2) . . ?
N1 C7 C1 119.85(19) . . ?
N5 C11 C10 123.5(2) . . ?
O1 C2 C1 122.6(2) . . ?
O1 C2 C3 117.5(2) . . ?
C3 C2 C1 119.9(2) . . ?
C10 C14 C13 119.6(2) . . ?
C5 C6 C1 121.7(2) . . ?
C12 C13 C14 118.1(3) . . ?
N5 C12 C13 124.4(2) . . ?
C4 C3 C2 120.4(2) . . ?
C6 C5 C4 119.0(3) . . ?
C3 C4 C5 120.8(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
O2 C8 1.246(2) . ?
N4 N3 1.380(2) . ?
N4 C9 1.281(2) . ?
O1 C2 1.359(3) . ?
N3 C8 1.357(3) . ?
N2 N1 1.377(2) . ?
N2 C8 1.349(3) . ?
N1 C7 1.277(2) . ?
N5 C11 1.338(2) . ?
N5 C12 1.339(3) . ?
C10 C9 1.455(3) . ?
C10 C11 1.394(3) . ?
C10 C14 1.379(3) . ?
C1 C7 1.447(3) . ?
C1 C2 1.402(3) . ?
C1 C6 1.391(3) . ?
C2 C3 1.387(3) . ?
C14 C13 1.385(3) . ?
C6 C5 1.378(3) . ?
C13 C12 1.364(4) . ?
C3 C4 1.367(3) . ?
C5 C4 1.380(3) . ?
