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_7241426
_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, H2 O'
_chemical_formula_sum            'C13 H13 N3 O4'
_chemical_formula_weight         275.26
_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
;
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                 99.089(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3319(3)
_cell_length_b                   12.7546(6)
_cell_length_c                   12.3732(7)
_cell_measurement_reflns_used    1457
_cell_measurement_temperature    293
_cell_measurement_theta_max      30.5780
_cell_measurement_theta_min      4.1450
_cell_volume                     1298.39(11)
_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 0.995
_diffrn_measurement_details
;
  1 omega   43.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       28.6542  179.0000 -120.0000 48

  2 omega  -46.00   30.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.3104   57.0000 -120.0000 76

  3 omega -107.00   19.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.3104  -19.0000  -90.0000 126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0422861000
_diffrn_orient_matrix_UB_12      0.0466667000
_diffrn_orient_matrix_UB_13      0.0178868000
_diffrn_orient_matrix_UB_21      0.0215223000
_diffrn_orient_matrix_UB_22      0.0066633000
_diffrn_orient_matrix_UB_23      -0.0528130000
_diffrn_orient_matrix_UB_31      -0.0720304000
_diffrn_orient_matrix_UB_32      0.0293982000
_diffrn_orient_matrix_UB_33      -0.0162728000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4884
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         4.148
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99245
_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    1.408
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method acetone
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0417P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.1021
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1606
_reflns_number_total             2403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra06845d2.cif
_cod_data_source_block           1bH2O
_cod_database_code               7241426
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C10 H16 N3 O6 Cu1'
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.966
_reflns_odcompleteness_completeness 99.59
_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 O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C10(H10), C8(H8), C2(H2A), C11(H11), C5(H5), C7(H7), C13(H13), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_shelx_res_checksum              84883
_olex2_date_sample_data_collection 2018-04-25
_olex2_exptl_crystal_mounting_method 'glass needle'
_olex2_submission_special_instructions 'No special instructions were received'