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_7241432
_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 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             2020-01-08
_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                 99.252(5)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   24.7095(14)
_cell_length_b                   10.1996(7)
_cell_length_c                   20.7620(14)
_cell_measurement_reflns_used    2580
_cell_measurement_temperature    293
_cell_measurement_theta_max      30.4170
_cell_measurement_theta_min      4.4520
_cell_volume                     5164.5(6)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -48.00   38.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.4667   19.0000   30.0000 86

  2 omega   47.00   82.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       28.8104  179.0000 -120.0000 35

  3 omega   34.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       28.8104  179.0000    0.0000 75

  4 omega  -77.00  -26.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.4667  -57.0000   60.0000 51

  5 omega  -92.00  -51.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.4667 -179.0000   90.0000 41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0179852000
_diffrn_orient_matrix_UB_12      0.0546384000
_diffrn_orient_matrix_UB_13      -0.0040014000
_diffrn_orient_matrix_UB_21      -0.0055268000
_diffrn_orient_matrix_UB_22      -0.0089408000
_diffrn_orient_matrix_UB_23      0.0321980000
_diffrn_orient_matrix_UB_31      0.0221482000
_diffrn_orient_matrix_UB_32      0.0421455000
_diffrn_orient_matrix_UB_33      0.0120713000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21864
_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         4.194
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98562
_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    1.396
_exptl_crystal_description       prism
_exptl_crystal_F_000             2272
_exptl_crystal_recrystallization_method methanol
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     733
_refine_ls_number_reflns         9550
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.1312
_refine_ls_R_factor_gt           0.0598
_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^)+(0.0399P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1427
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4915
_reflns_number_total             9550
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra06845d2.cif
_cod_data_source_block           4a
_cod_database_code               7241432
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.936
_reflns_odcompleteness_completeness 99.58
_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:
 N13(H13A,H13B), N23(H23A,H23B), N33(H33A,H33B), N43(H43A,H43B)
2.b Aromatic/amide H refined with riding coordinates:
 N11(H11), N41(H41), N21(H21), N31(H31), C12(H12A), C210(H210), C32(H32A),
 C42(H42A), C214(H214), C48(H48), C22(H22A), C211(H211), C111(H111), C114(H114),
  C110(H110), C47(H47), C113(H113), C46(H46), C38(H38), C18(H18), C28(H28),
 C213(H213), C410(H410), C26(H26), C27(H27), C36(H36), C37(H37), C16(H16),
 C17(H17), C314(H314), C310(H310), C414(H414), C411(H411), C311(H311),
 C413(H413), C313(H313)
2.c Idealised tetrahedral OH refined as rotating group:
 O42(H42), O43(H43), O32(H32), O12(H12), O22(H22), O23(H23), O33(H33), O13(H13)
;
_shelx_res_checksum              64366
_olex2_date_sample_data_collection 2018-05-29
_olex2_exptl_crystal_mounting_method 'glass needle'
_olex2_submission_special_instructions 'No special instructions were received'