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_7241431
_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 H13 N3 O3'
_chemical_formula_sum            'C14 H13 N3 O3'
_chemical_formula_weight         271.27
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-08
_audit_creation_method
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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                 97.757(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5511(6)
_cell_length_b                   22.351(3)
_cell_length_c                   9.0707(12)
_cell_measurement_reflns_used    775
_cell_measurement_temperature    293
_cell_measurement_theta_max      24.2340
_cell_measurement_theta_min      4.2740
_cell_volume                     1316.0(3)
_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
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega    9.00   88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       28.6542   57.0000 -150.0000 79

  2 omega   81.00  107.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       28.6542  179.0000  -30.0000 26

  3 omega  -82.00   34.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.3104  -19.0000 -120.0000 116

  4 omega -110.00  -75.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.3104 -179.0000 -150.0000 35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0047893000
_diffrn_orient_matrix_UB_12      -0.0105266000
_diffrn_orient_matrix_UB_13      -0.0742100000
_diffrn_orient_matrix_UB_21      -0.0293374000
_diffrn_orient_matrix_UB_22      0.0289709000
_diffrn_orient_matrix_UB_23      -0.0270320000
_diffrn_orient_matrix_UB_31      0.1050674000
_diffrn_orient_matrix_UB_32      0.0075417000
_diffrn_orient_matrix_UB_33      0.0001496000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5134
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.492
_diffrn_reflns_theta_min         4.164
_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  0.98305
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_recrystallization_method acetonitrile
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2427
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0586
_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^)+(0.0809P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1809
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1418
_reflns_number_total             2427
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra06845d2.cif
_cod_data_source_block           3b
_cod_database_code               7241431
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.940
_reflns_odcompleteness_completeness 99.64
_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, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Rotating group:
 N3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C2(H2A), C7(H7), C8(H8), C14(H14), C13(H13), C11(H11), C12(H12)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O2(H2)
;
_shelx_res_checksum              19537
_olex2_date_sample_data_collection 2018-05-29
_olex2_submission_special_instructions 'No special instructions were received'