Effective methods for the synthesis of hydrazones, quinazolines, and Schiff bases: reaction monitoring using a chemometric approach
Pisk, Jana; Đilović, Ivica; Hrenar, Tomica; Cvijanović, Danijela; Pavlović, Gordana; Vrdoljak, Višnja; RSC Advances 10 (2020) 38566–38577; doi:10.1039/D0RA06845D

data_7241427
_publ_section_title
;
 Effective methods for the synthesis of hydrazones, quinazolines, and
 Schiff bases: reaction monitoring using a chemometric approach
;
_journal_issue                   63
_journal_name_full               'RSC Advances'
_journal_page_first              38566
_journal_page_last               38577
_journal_paper_doi               10.1039/D0RA06845D
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C14 H12 N2 O4, H2 O'
_chemical_formula_sum            'C14 H14 N2 O5'
_chemical_formula_weight         290.27
_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             2020-01-09
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-02-20 deposited with the CCDC.	2020-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.876(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2515(4)
_cell_length_b                   6.7577(2)
_cell_length_c                   13.2137(3)
_cell_measurement_reflns_used    2819
_cell_measurement_temperature    293
_cell_measurement_theta_max      75.9540
_cell_measurement_theta_min      2.9580
_cell_volume                     1332.72(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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   -115.00 -67.00   1.00    1.00    --  -41.74 -38.00  30.00   48
  2  \w    -82.00 -48.00   1.00    1.00    --  -41.74 -57.00 -30.00   34
  3  \w    -93.00 -21.00   1.00    1.00    --  -41.74 126.00-150.00   72
  4  \w    -52.00 -24.00   1.00    1.00    --  -41.74 -38.00  30.00   28
  5  \w      9.00  70.00   1.00    1.00    --   41.74 -57.00   0.00   61
  6  \w     40.00 139.00   1.00    4.00    --  111.00 -61.00-180.00   99
  7  \w    103.00 154.00   1.00    4.00    --  111.00  30.00-120.00   51
  8  \w    146.00 175.00   1.00    4.00    --  111.00  61.00 -30.00   29
  9  \w     84.00 145.00   1.00    4.00    --  111.00  30.00  90.00   61
 10  \w     50.00 106.00   1.00    4.00    --  111.00 -95.00  60.00   56
 11  \w     88.00 138.00   1.00    4.00    --  111.00  61.00 -30.00   50
 12  \w     49.00 104.00   1.00    4.00    --  111.00 -95.00  90.00   55
 13  \w     51.00  88.00   1.00    4.00    --  111.00 -30.00-120.00   37
 14  \w    101.00 138.00   1.00    4.00    --  111.00 -30.00-120.00   37
 15  \w     93.00 166.00   1.00    4.00    --  111.00  30.00 -60.00   73
 16  \w    141.00 169.00   1.00    4.00    --  111.00  61.00 -60.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0147410000
_diffrn_orient_matrix_UB_12      0.0292279000
_diffrn_orient_matrix_UB_13      0.1179257000
_diffrn_orient_matrix_UB_21      -0.0698093000
_diffrn_orient_matrix_UB_22      -0.1621522000
_diffrn_orient_matrix_UB_23      0.0057790000
_diffrn_orient_matrix_UB_31      0.0745949000
_diffrn_orient_matrix_UB_32      -0.1574987000
_diffrn_orient_matrix_UB_33      0.0159370000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5738
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.995
_diffrn_reflns_theta_max         66.995
_diffrn_reflns_theta_min         2.961
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.941
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.447
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2347
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0499
_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/[\s^2^(Fo^2^)+(0.1049P)^2^+0.0756P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1444
_refine_ls_wR_factor_ref         0.1531
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1991
_reflns_number_total             2347
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra06845d2.cif
_cod_data_source_block           5bH2O
_cod_database_code               7241427
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.856
_shelx_estimated_absorpt_t_min   0.656
_reflns_odcompleteness_completeness 99.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C13(H13), C8(H8), C5(H5), C11(H11), C2(H2A), C14(H14), C1(H1A)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1), O4(H4), O3(H3)
;
_shelx_res_checksum              79945
_olex2_exptl_crystal_mounting_method 'glass needle'
_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 1.384
_oxdiff_exptl_absorpt_empirical_full_min 0.720