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_7241424
_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         'C13 H11 N3 O3, C H4 O'
_chemical_formula_sum            'C14 H15 N3 O4'
_chemical_formula_weight         289.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-20 deposited with the CCDC.	2020-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.924(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4964(4)
_cell_length_b                   14.0972(6)
_cell_length_c                   11.1992(5)
_cell_measurement_reflns_used    11502
_cell_measurement_temperature    150
_cell_measurement_theta_max      32.4640
_cell_measurement_theta_min      4.2820
_cell_volume                     1334.23(10)
_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      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega   -3.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   77.0000  -90.0000 92

  2 omega   -3.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   77.0000   90.0000 92

  3 omega    7.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   57.0000   30.0000 81

  4 omega    7.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   57.0000 -150.0000 81

  5 omega  -43.00   37.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -57.0000  120.0000 80

  6 omega  -46.00   40.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -37.0000   30.0000 86

  7 omega  -46.00   40.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -37.0000 -150.0000 86

  8 omega  -25.00   59.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -99.0000   30.0000 84

  9 omega  -25.00   59.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -99.0000 -180.0000 84

 10 omega  -25.00   59.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -99.0000   90.0000 84

 11 omega  -25.00   59.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -99.0000  -60.0000 84

 12 omega  -44.00   48.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -77.0000  -30.0000 92

 13 omega    7.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   57.0000  -60.0000 81

 14 omega   34.00   93.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  179.0000   30.0000 59

 15 omega   -3.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   77.0000  150.0000 92

 16 omega  -25.00   59.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -99.0000 -120.0000 84

 17 omega   -3.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   77.0000  -30.0000 92

 18 omega  -81.00   -3.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4994  135.0000  116.0202 78

 19 omega  -86.00   -8.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4994  143.0000 -172.7514 78

 20 omega  -63.00   19.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4994  106.0000   13.0979 82

 21 omega  -80.00   -3.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4994  134.0000  -78.1012 77

 22 omega  -71.00    8.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4994  119.0000   34.8401 79

 23 omega  -60.00  -17.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4994  100.0000  154.7040 43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0659397000
_diffrn_orient_matrix_UB_12      -0.0064189000
_diffrn_orient_matrix_UB_13      -0.0435456000
_diffrn_orient_matrix_UB_21      0.0486939000
_diffrn_orient_matrix_UB_22      -0.0246913000
_diffrn_orient_matrix_UB_23      -0.0373795000
_diffrn_orient_matrix_UB_31      -0.0179901000
_diffrn_orient_matrix_UB_32      -0.0433641000
_diffrn_orient_matrix_UB_33      0.0276202000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            45731
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         4.293
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97389
_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            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_recrystallization_method methanol
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2464
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0390
_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/[\s^2^(Fo^2^)+(0.0660P)^2^+0.2108P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1083
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2092
_reflns_number_total             2464
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra06845d2.cif
_cod_data_source_block           1aMeOH
_cod_database_code               7241424
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C20 N4 O5'
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.976
_reflns_odcompleteness_completeness 99.65
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C13(H13), C2(H2A), C8(H8), C6(H6), C10(H10), C11(H11), C7(H7), C12(H12)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O2(H2), O3(H3)
;
_shelx_res_checksum              76728
_olex2_date_sample_data_collection 2019-01-16
_olex2_exptl_crystal_mounting_method loop
_olex2_submission_special_instructions 'No special instructions were received'