#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:28:18 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257835 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/98/7059809.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_7059809
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'
_chemical_formula_sum            'C14 H13 N5 O2'
_chemical_formula_weight         283.29
_chemical_name_systematic
3-[(E)-[(1-hydroxyphenyl-2-yl)methylidene]amino]-1-[(E)-[(pyridin-4-yl)methylidene]amino]urea
_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
_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                93.758(5)
_cell_angle_beta                 93.790(5)
_cell_angle_gamma                92.877(5)
_cell_formula_units_Z            2
_cell_length_a                   7.7355(5)
_cell_length_b                   9.1187(5)
_cell_length_c                   9.7039(5)
_cell_measurement_reflns_used    2852
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.5280
_cell_measurement_theta_min      4.6210
_cell_volume                     680.50(7)
_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 0.924
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    7.00   88.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   57.0000 -120.0000 81

#__ type_ start__ end____ width___ exp.time_
  2 omega    7.00   88.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   57.0000   90.0000 81

#__ type_ start__ end____ width___ exp.time_
  3 omega  -25.00   59.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -99.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega  -43.00   37.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -57.0000 -180.0000 80

#__ type_ start__ end____ width___ exp.time_
  5 omega  -43.00   37.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -57.0000    0.0000 80

#__ type_ start__ end____ width___ exp.time_
  6 omega  -44.00   48.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -77.0000  120.0000 92

#__ type_ start__ end____ width___ exp.time_
  7 omega   -3.00   89.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   77.0000 -120.0000 92

#__ type_ start__ end____ width___ exp.time_
  8 omega    7.00   88.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   57.0000 -180.0000 81

#__ type_ start__ end____ width___ exp.time_
  9 omega  -25.00   59.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -99.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
 10 omega    7.00   84.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432 -140.0000  136.0000 77

#__ type_ start__ end____ width___ exp.time_
 11 omega  -25.00   59.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -99.0000 -150.0000 84

#__ type_ start__ end____ width___ exp.time_
 12 omega   -3.00   89.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   77.0000  -30.0000 92

#__ type_ start__ end____ width___ exp.time_
 13 omega  -46.00   40.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -37.0000 -180.0000 86

#__ type_ start__ end____ width___ exp.time_
 14 omega   -3.00   89.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   77.0000  120.0000 92

#__ type_ start__ end____ width___ exp.time_
 15 omega    1.00   78.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432 -130.0000  -50.0000 77

#__ type_ start__ end____ width___ exp.time_
 16 omega  -85.00  -35.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4994  141.0000   92.7182 50

#__ type_ start__ end____ width___ exp.time_
 17 omega  -86.00   -8.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4994  142.0000  -10.7523 78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0071401000
_diffrn_orient_matrix_UB_12      0.0127650000
_diffrn_orient_matrix_UB_13      -0.0707730000
_diffrn_orient_matrix_UB_21      0.0274400000
_diffrn_orient_matrix_UB_22      0.0744125000
_diffrn_orient_matrix_UB_23      0.0188612000
_diffrn_orient_matrix_UB_31      0.0875561000
_diffrn_orient_matrix_UB_32      -0.0198682000
_diffrn_orient_matrix_UB_33      0.0052350000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25951
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.919
_diffrn_reflns_theta_min         4.220
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94687
_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_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       prism
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1506
_refine_ls_R_factor_gt           0.0625
_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)+(0.0626P)²+0.0121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1634
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2221
_reflns_number_total             4700
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj03106b2.cif
_cod_data_source_block           H2L4pysal
_cod_depositor_comments
;Adding full bibliography for 7059802--7059812.cif.

 Adding full bibliography for 7059802--7059812.cif.
;
_cod_database_code               7059809
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H15 Mo N5 O4'
_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   0.990
_shelx_estimated_absorpt_t_min   0.962
_reflns_odcompleteness_completeness 99.71
_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) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C9(H9), C7(H7), C12(H12), C14(H14), C13(H13), C6(H6), C3(H3A),
 C4(H4), C5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O2 O 0.12808(14) 0.35292(13) 0.56518(11) 0.0584(3) Uani 1 1 d . . . . .
O1 O 0.40255(15) 0.07397(15) 0.75162(14) 0.0668(4) Uani 1 1 d . . . . .
N4 N 0.21794(16) 0.46661(15) 0.23918(13) 0.0496(4) Uani 1 1 d . . . . .
N1 N 0.43549(17) 0.23676(14) 0.54169(13) 0.0473(3) Uani 1 1 d . . . . .
N2 N 0.36835(18) 0.32475(16) 0.44404(14) 0.0528(4) Uani 1 1 d . . . . .
N3 N 0.14227(18) 0.45819(18) 0.36256(14) 0.0577(4) Uani 1 1 d . . . . .
N5 N 0.35530(18) 0.60934(17) -0.23623(14) 0.0586(4) Uani 1 1 d . . . . .
C10 C 0.22109(18) 0.57305(17) 0.02231(15) 0.0434(4) Uani 1 1 d . . . . .
C11 C 0.2979(2) 0.45977(18) -0.04837(15) 0.0473(4) Uani 1 1 d . . . . .
H11 H 0.306042 0.368917 -0.010830 0.057 Uiso 1 1 calc R . . . .
C9 C 0.15638(19) 0.55990(18) 0.15935(16) 0.0479(4) Uani 1 1 d . . . . .
H9 H 0.070042 0.619720 0.188478 0.057 Uiso 1 1 calc R . . . .
C8 C 0.2092(2) 0.37507(18) 0.46280(16) 0.0487(4) Uani 1 1 d . . . . .
C1 C 0.6700(2) 0.11140(17) 0.63928(17) 0.0483(4) Uani 1 1 d . . . . .
C7 C 0.5942(2) 0.20404(17) 0.53826(16) 0.0502(4) Uani 1 1 d . . . . .
H7 H 0.661343 0.239939 0.470520 0.060 Uiso 1 1 calc R . . . .
C12 C 0.3623(2) 0.48251(19) -0.17505(16) 0.0530(4) Uani 1 1 d . . . . .
H12 H 0.413588 0.404823 -0.220555 0.064 Uiso 1 1 calc R . . . .
C2 C 0.5738(2) 0.05024(18) 0.74160(17) 0.0504(4) Uani 1 1 d . . . . .
C14 C 0.2077(2) 0.70385(18) -0.04235(17) 0.0539(4) Uani 1 1 d . . . . .
H14 H 0.152532 0.781915 -0.001044 0.065 Uiso 1 1 calc R . . . .
C13 C 0.2771(2) 0.7165(2) -0.16849(18) 0.0616(5) Uani 1 1 d . . . . .
H13 H 0.268861 0.805650 -0.209142 0.074 Uiso 1 1 calc R . . . .
C6 C 0.8447(2) 0.0822(2) 0.6382(2) 0.0674(5) Uani 1 1 d . . . . .
H6 H 0.911091 0.122797 0.572332 0.081 Uiso 1 1 calc R . . . .
C3 C 0.6520(2) -0.03830(19) 0.8354(2) 0.0653(5) Uani 1 1 d . . . . .
H3A H 0.587551 -0.079408 0.902216 0.078 Uiso 1 1 calc R . . . .
C4 C 0.8248(3) -0.0655(2) 0.8298(2) 0.0770(6) Uani 1 1 d . . . . .
H4 H 0.876335 -0.125368 0.892883 0.092 Uiso 1 1 calc R . . . .
C5 C 0.9220(3) -0.0053(2) 0.7323(3) 0.0834(7) Uani 1 1 d . . . . .
H5 H 1.039018 -0.023416 0.729710 0.100 Uiso 1 1 calc R . . . .
H2 H 0.429(3) 0.347(2) 0.379(2) 0.100 Uiso 1 1 d R . . . .
H3 H 0.049(3) 0.513(2) 0.383(2) 0.100 Uiso 1 1 d R . . . .
H1 H 0.373(3) 0.134(3) 0.686(2) 0.100 Uiso 1 1 d R . . . .
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 115.51(13) . . ?
C7 N1 N2 118.67(13) . . ?
C8 N2 N1 116.99(13) . . ?
C8 N3 N4 120.91(14) . . ?
C13 N5 C12 115.83(14) . . ?
C11 C10 C9 122.90(14) . . ?
C11 C10 C14 117.04(14) . . ?
C14 C10 C9 120.05(15) . . ?
C12 C11 C10 119.54(14) . . ?
N4 C9 C10 120.24(14) . . ?
O2 C8 N2 123.60(14) . . ?
O2 C8 N3 120.21(14) . . ?
N2 C8 N3 116.16(13) . . ?
C2 C1 C7 122.43(14) . . ?
C6 C1 C7 119.79(15) . . ?
C6 C1 C2 117.77(15) . . ?
N1 C7 C1 120.41(14) . . ?
N5 C12 C11 123.98(16) . . ?
O1 C2 C1 121.96(14) . . ?
O1 C2 C3 117.78(15) . . ?
C3 C2 C1 120.25(15) . . ?
C13 C14 C10 119.15(16) . . ?
N5 C13 C14 124.40(15) . . ?
C5 C6 C1 121.71(18) . . ?
C4 C3 C2 120.06(18) . . ?
C5 C4 C3 120.77(17) . . ?
C4 C5 C6 119.43(17) . . ?
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 1.2318(17) . ?
O1 C2 1.3617(19) . ?
N4 N3 1.3719(17) . ?
N4 C9 1.2762(19) . ?
N1 N2 1.3740(18) . ?
N1 C7 1.2802(19) . ?
N2 C8 1.355(2) . ?
N3 C8 1.3630(19) . ?
N5 C12 1.336(2) . ?
N5 C13 1.334(2) . ?
C10 C11 1.383(2) . ?
C10 C9 1.462(2) . ?
C10 C14 1.389(2) . ?
C11 C12 1.381(2) . ?
C1 C7 1.449(2) . ?
C1 C2 1.407(2) . ?
C1 C6 1.391(2) . ?
C2 C3 1.385(2) . ?
C14 C13 1.378(2) . ?
C6 C5 1.378(3) . ?
C3 C4 1.376(3) . ?
C4 C5 1.372(3) . ?
