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_7241425
_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         'C21 H17 N3 O5, C H4 O'
_chemical_formula_sum            'C22 H21 N3 O6'
_chemical_formula_weight         423.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-25 deposited with the CCDC.	2020-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.637(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.8673(7)
_cell_length_b                   10.0421(4)
_cell_length_c                   24.2618(12)
_cell_measurement_reflns_used    1730
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      31.8010
_cell_measurement_theta_min      4.1510
_cell_volume                     3864.3(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      293.15
_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 -102.00  -40.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.1542  -57.0000   30.0000 62

  2 omega -110.00  -43.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.1542 -179.0000   30.0000 67

  3 omega  -97.00   33.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.1542  -19.0000 -150.0000 130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0352216000
_diffrn_orient_matrix_UB_12      0.0153543000
_diffrn_orient_matrix_UB_13      0.0175163000
_diffrn_orient_matrix_UB_21      -0.0146350000
_diffrn_orient_matrix_UB_22      -0.0454998000
_diffrn_orient_matrix_UB_23      0.0199436000
_diffrn_orient_matrix_UB_31      0.0233248000
_diffrn_orient_matrix_UB_32      -0.0517984000
_diffrn_orient_matrix_UB_33      -0.0123013000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7907
_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         25.995
_diffrn_reflns_theta_min         4.145
_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  0.99636
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_recrystallization_method 'From methanol'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         3784
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0595
_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^)+(0.0563P)^2^+2.8691P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1445
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2584
_reflns_number_total             3784
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra06845d2.cif
_cod_data_source_block           3c
_cod_database_code               7241425
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.977
_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. Restrained distances
 C22B-O22B
 1.45 with sigma of 0.0001
 C22A-O22A
 1.45 with sigma of 0.0001
 O4-H4
 0.82 with sigma of 0.001
 O3-H3
 0.82 with sigma of 0.0001
3. Rigid bond restraints
 C22B, C22A
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
C22B \\sim C22A: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04
Uanis(C22B) \\sim Ueq, Uanis(C22A) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.04
5. Others
 Sof(C22A)=Sof(H22E)=Sof(H22F)=Sof(H22G)=Sof(O22A)=Sof(H22H)=1-FVAR(1)
 Sof(C22B)=Sof(H22A)=Sof(H22B)=Sof(H22C)=Sof(O22B)=Sof(H22D)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C15(H15)
6.b Aromatic/amide H refined with riding coordinates:
 N3(H3A), C2(H2A), C6(H6), C14(H14), C11(H11), C8(H8), C21(H21), C7(H7),
 C19(H19), C13(H13), C12(H12), C20(H20)
6.c Idealised Me refined as rotating group:
 C22B(H22A,H22B,H22C), C22A(H22E,H22F,H22G)
6.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O5(H5), O22B(H22D), O22A(H22H)
;
_shelx_res_checksum              73606
_olex2_submission_special_instructions 'No special instructions were received'