A long-range tautomeric effect on a new Schiff isoniazid analogue, evidenced by NMR study and X-ray crystallography
Tănase, Constantin I.; Drăghici, Constantin; Shova, Sergiu; Hanganu, Anamaria; Gal, Emese; Munteanu, Cristian V. A.; New Journal of Chemistry 42 (2018) 14459–; doi:10.1039/C8NJ01680A

data_7057583
_publ_section_title
;
 A long-range tautomeric effect on a new Schiff isoniazid analogue,
 evidenced by NMR study and X-ray crystallography
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14459
_journal_paper_doi               10.1039/C8NJ01680A
_journal_volume                  42
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         '4(C10 H13 N3 O2), 4(H2 O)'
_chemical_formula_sum            'C40 H60 N12 O12'
_chemical_formula_weight         901.00
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-07-09 deposited with the CCDC.
2018-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                110.945(4)
_cell_angle_beta                 98.955(3)
_cell_angle_gamma                92.334(3)
_cell_formula_units_Z            1
_cell_length_a                   6.6116(2)
_cell_length_b                   12.1182(5)
_cell_length_c                   15.0179(7)
_cell_measurement_reflns_used    5949
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      29.0250
_cell_measurement_theta_min      1.7990
_cell_volume                     1103.97(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0797
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -19.00  21.00   1.00    5.00    --  -15.76 -99.00  30.00   40
  2  \w    -24.00  17.00   1.00    5.00    --  -15.76 -99.00 -90.00   41
  3  \w    -42.00  84.00   1.00    5.00    --   17.94   0.00-150.00  126
  4  \w      0.00  69.00   1.00    5.00    --   17.94  38.00 -90.00   69
  5  \w      4.00  38.00   1.00    5.00    --   17.94 -77.00 150.00   34
  6  \w    -88.00 -39.00   1.00    5.00    --  -15.76-178.00 -90.00   49
  7  \w    -64.00 -14.00   1.00    5.00    --  -15.44 116.00-122.00   50
  8  \w    -25.00  22.00   1.00    5.00    --  -15.44 -99.00 120.00   47
  9  \w    -23.00   3.00   1.00    5.00    --  -15.44 -99.00   0.00   26
 10  \w     53.00  79.00   1.00    5.00    --   17.79  57.00 -30.00   26
 11  \w      3.00  37.00   1.00    5.00    --   17.79  57.00 -30.00   34
 12  \w     30.00  57.00   1.00    5.00    --   17.79 -99.00  60.00   27
 13  \w     10.00  57.00   1.00    5.00    --   17.79 -99.00-120.00   47
 14  \w    -30.00  20.00   1.00    5.00    --   17.79 -57.00  60.00   50
 15  \w    -51.00  -1.00   1.00    5.00    --   17.79   0.00  90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0327156000
_diffrn_orient_matrix_UB_12      -0.0372574000
_diffrn_orient_matrix_UB_13      -0.0493816000
_diffrn_orient_matrix_UB_21      -0.0212669000
_diffrn_orient_matrix_UB_22      0.0505224000
_diffrn_orient_matrix_UB_23      -0.0118333000
_diffrn_orient_matrix_UB_31      0.1020013000
_diffrn_orient_matrix_UB_32      0.0056338000
_diffrn_orient_matrix_UB_33      -0.0082582000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16607
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.48
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         7727
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0455
_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/[\s^2^(Fo^2^)+(0.0453P)^2^+0.0368P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0978
_reflns_number_gt                6834
_reflns_number_total             7727
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8nj01680a2.cif
_cod_data_source_block           shi_3363_cota
_cod_depositor_comments          'Adding full bibliography for 7057583.cif.'
_cod_original_cell_volume        1103.98(7)
_cod_database_code               7057583
_chemical_oxdiff_formula         'C10 H10 N3 O1'
_chemical_oxdiff_usercomment     TVC_3416
_reflns_odcompleteness_completeness 99.98
_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 Riding coordinates:
 O2A(H2A), O2C(H2C), O2B(H2B), O2D(H2D), O1W(H1WA,H1WB), O3W(H3WA,H3WB),
 O2W(H2WA,H2WB), O4W(H4WA,H4WB)
2.b Secondary CH2 refined with riding coordinates:
 C8A(H8AA,H8AB), C9A(H9AA,H9AB), C10A(H10A,H10B), C8C(H8CA,H8CB), C9C(H9CA,
 H9CB), C10C(H10C,H10D), C8B(H8BA,H8BB), C9B(H9BA,H9BB), C10B(H10E,H10F),
 C8D(H8DA,H8DB), C9D(H9DA,H9DB), C10D(H10G,H10H)
2.c Aromatic/amide H refined with riding coordinates:
 N2A(H2AA), C1A(H1A), C2A(H2AB), C4A(H4A), C5A(H5A), C7A(H7A), N2C(H2CA),
 C1C(H1C), C2C(H2CB), C4C(H4C), C5C(H5C), C7C(H7C), N2B(H2BA), C1B(H1B),
 C2B(H2BB), C4B(H4B), C5B(H5B), C7B(H7B), N2D(H2DA), C1D(H1D), C2D(H2DB),
 C4D(H4D), C5D(H5D), C7D(H7D)
;
_olex2_date_sample_data_collection 2016-12-13
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.136
_oxdiff_exptl_absorpt_empirical_full_min 0.807