#------------------------------------------------------------------------------
#$Date: 2025-08-23 01:35:05 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301870 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/14/7241424.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7241424
loop_
_publ_author_name
'Pisk, Jana'
'Đilović, Ivica'
'Hrenar, Tomica'
'Cvijanović, Danijela'
'Pavlović, Gordana'
'Vrdoljak, Višnja'
_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
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -3.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   77.0000  -90.0000 92

#__ type_ start__ end____ width___ exp.time_
  2 omega   -3.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   77.0000   90.0000 92

#__ type_ start__ end____ width___ exp.time_
  3 omega    7.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   57.0000   30.0000 81

#__ type_ start__ end____ width___ exp.time_
  4 omega    7.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   57.0000 -150.0000 81

#__ type_ start__ end____ width___ exp.time_
  5 omega  -43.00   37.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -57.0000  120.0000 80

#__ type_ start__ end____ width___ exp.time_
  6 omega  -46.00   40.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -37.0000   30.0000 86

#__ type_ start__ end____ width___ exp.time_
  7 omega  -46.00   40.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -37.0000 -150.0000 86

#__ type_ start__ end____ width___ exp.time_
  8 omega  -25.00   59.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -99.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
  9 omega  -25.00   59.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -99.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
 10 omega  -25.00   59.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -99.0000   90.0000 84

#__ type_ start__ end____ width___ exp.time_
 11 omega  -25.00   59.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -99.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
 12 omega  -44.00   48.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -77.0000  -30.0000 92

#__ type_ start__ end____ width___ exp.time_
 13 omega    7.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   57.0000  -60.0000 81

#__ type_ start__ end____ width___ exp.time_
 14 omega   34.00   93.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  179.0000   30.0000 59

#__ type_ start__ end____ width___ exp.time_
 15 omega   -3.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   77.0000  150.0000 92

#__ type_ start__ end____ width___ exp.time_
 16 omega  -25.00   59.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -99.0000 -120.0000 84

#__ type_ start__ end____ width___ exp.time_
 17 omega   -3.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   77.0000  -30.0000 92

#__ type_ start__ end____ width___ exp.time_
 18 omega  -81.00   -3.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4994  135.0000  116.0202 78

#__ type_ start__ end____ width___ exp.time_
 19 omega  -86.00   -8.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4994  143.0000 -172.7514 78

#__ type_ start__ end____ width___ exp.time_
 20 omega  -63.00   19.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4994  106.0000   13.0979 82

#__ type_ start__ end____ width___ exp.time_
 21 omega  -80.00   -3.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4994  134.0000  -78.1012 77

#__ type_ start__ end____ width___ exp.time_
 22 omega  -71.00    8.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4994  119.0000   34.8401 79

#__ type_ start__ end____ width___ exp.time_
 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       'ω 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/[σ²(Fo²)+(0.0660P)²+0.2108P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_olex2_date_sample_data_collection 2019-01-16
_olex2_exptl_crystal_mounting_method loop
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.60942(12) 0.74726(7) 0.75137(9) 0.0328(3) Uani 1 1 d . . . . .
O4 O 0.66364(13) 0.70448(7) 0.51801(9) 0.0347(3) Uani 1 1 d . . . . .
H4 H 0.672712 0.724526 0.589018 0.052 Uiso 1 1 calc GR . . . .
O2 O 0.51286(11) 0.47856(7) 0.78570(9) 0.0303(3) Uani 1 1 d . . . . .
H2 H 0.507033 0.537889 0.790572 0.045 Uiso 1 1 calc GR . . . .
O3 O 0.50852(13) 0.29051(7) 0.79899(10) 0.0368(3) Uani 1 1 d . . . . .
H3 H 0.498880 0.232039 0.810689 0.055 Uiso 1 1 calc GR . . . .
N1 N 0.40477(13) 0.73792(8) 0.86523(10) 0.0240(3) Uani 1 1 d . . . . .
H1 H 0.337144 0.767744 0.906425 0.029 Uiso 1 1 calc R . . . .
N2 N 0.40456(13) 0.64054(8) 0.85702(10) 0.0245(3) Uani 1 1 d . . . . .
N3 N 0.50033(14) 1.09133(8) 0.82666(10) 0.0288(3) Uani 1 1 d . . . . .
C9 C 0.50611(15) 0.89257(9) 0.81960(11) 0.0224(3) Uani 1 1 d . . . . .
C3 C 0.30821(15) 0.49215(9) 0.91997(12) 0.0232(3) Uani 1 1 d . . . . .
C4 C 0.40926(15) 0.43835(9) 0.85483(12) 0.0231(3) Uani 1 1 d . . . . .
C1 C 0.51220(16) 0.78646(10) 0.80801(11) 0.0237(3) Uani 1 1 d . . . . .
C13 C 0.63258(17) 0.94584(10) 0.78650(12) 0.0283(3) Uani 1 1 d . . . . .
H13 H 0.722944 0.915463 0.760659 0.034 Uiso 1 1 calc R . . . .
C2 C 0.31203(16) 0.59533(9) 0.92069(12) 0.0245(3) Uani 1 1 d . . . . .
H2A H 0.245542 0.629522 0.968644 0.029 Uiso 1 1 calc R . . . .
C5 C 0.40428(16) 0.33882(9) 0.86051(12) 0.0252(3) Uani 1 1 d . . . . .
C8 C 0.20276(16) 0.44607(10) 0.98852(13) 0.0280(3) Uani 1 1 d . . . . .
H8 H 0.135128 0.482373 1.033253 0.034 Uiso 1 1 calc R . . . .
C6 C 0.29724(17) 0.29568(9) 0.92771(13) 0.0281(3) Uani 1 1 d . . . . .
H6 H 0.292618 0.228382 0.930240 0.034 Uiso 1 1 calc R . . . .
C10 C 0.37835(16) 0.94104(10) 0.85764(12) 0.0256(3) Uani 1 1 d . . . . .
H10 H 0.290368 0.907380 0.882254 0.031 Uiso 1 1 calc R . . . .
C11 C 0.38088(17) 1.03907(10) 0.85923(13) 0.0281(3) Uani 1 1 d . . . . .
H11 H 0.292178 1.071230 0.885094 0.034 Uiso 1 1 calc R . . . .
C7 C 0.19613(17) 0.34824(10) 0.99172(13) 0.0310(3) Uani 1 1 d . . . . .
H7 H 0.123088 0.317193 1.037282 0.037 Uiso 1 1 calc R . . . .
C12 C 0.62451(17) 1.04391(10) 0.79186(13) 0.0300(3) Uani 1 1 d . . . . .
H12 H 0.711840 1.079506 0.769631 0.036 Uiso 1 1 calc R . . . .
C14 C 0.54359(19) 0.63364(11) 0.50421(15) 0.0384(4) Uani 1 1 d . . . . .
H14A H 0.498784 0.631028 0.420056 0.058 Uiso 1 1 calc GR . . . .
H14B H 0.459933 0.649283 0.554970 0.058 Uiso 1 1 calc GR . . . .
H14C H 0.589448 0.571858 0.528106 0.058 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 117.97(11) . . ?
C2 N2 N1 117.05(11) . . ?
C11 N3 C12 116.59(12) . . ?
C13 C9 C1 118.66(12) . . ?
C10 C9 C1 123.52(12) . . ?
C10 C9 C13 117.79(12) . . ?
C4 C3 C2 121.88(12) . . ?
C8 C3 C4 119.65(12) . . ?
C8 C3 C2 118.46(12) . . ?
O2 C4 C3 122.59(12) . . ?
O2 C4 C5 117.90(12) . . ?
C3 C4 C5 119.51(12) . . ?
O1 C1 N1 122.76(12) . . ?
O1 C1 C9 121.68(12) . . ?
N1 C1 C9 115.55(11) . . ?
C12 C13 C9 118.92(13) . . ?
N2 C2 C3 120.52(12) . . ?
O3 C5 C4 116.92(12) . . ?
O3 C5 C6 123.78(12) . . ?
C6 C5 C4 119.29(12) . . ?
C7 C8 C3 120.54(13) . . ?
C5 C6 C7 121.60(12) . . ?
C11 C10 C9 119.02(12) . . ?
N3 C11 C10 124.02(13) . . ?
C8 C7 C6 119.38(13) . . ?
N3 C12 C13 123.65(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2241(16) . ?
O4 C14 1.4245(18) . ?
O2 C4 1.3550(16) . ?
O3 C5 1.3597(16) . ?
N1 N2 1.3759(15) . ?
N1 C1 1.3538(17) . ?
N2 C2 1.2839(17) . ?
N3 C11 1.3350(18) . ?
N3 C12 1.3405(18) . ?
C9 C1 1.5028(18) . ?
C9 C13 1.3923(19) . ?
C9 C10 1.3865(19) . ?
C3 C4 1.4049(18) . ?
C3 C2 1.4550(18) . ?
C3 C8 1.3986(18) . ?
C4 C5 1.4054(19) . ?
C13 C12 1.386(2) . ?
C5 C6 1.3801(19) . ?
C8 C7 1.381(2) . ?
C6 C7 1.389(2) . ?
C10 C11 1.3821(19) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168341720
