Synthesis and computationally assisted spectroscopic study of tautomerism in 3-(phenyl(2-arylhydrazineylidene)methyl)quinoxalin-2(1H)-ones
Katsyuba, Sergey A.; Mustakimova, Liliya V.; Gerasimova, Tatiana P.; Burganov, Timur I.; Sirazieva, Aisylu R.; Voronina, Julia K.; Shamsutdinova, Leisan R.; Rizvanov, Il’dar Kh.; Mamedov, Vakhid A.; New Journal of Chemistry 46 (2022) 17889–17902; doi:10.1039/D2NJ03499A

data_7061833
_publ_section_title
;
 Synthesis and computationally assisted spectroscopic study of tautomerism
 in 3-(phenyl(2-arylhydrazineylidene)methyl)quinoxalin-2(1H)-ones
;
_journal_issue                   37
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17889
_journal_page_last               17902
_journal_paper_doi               10.1039/D2NJ03499A
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         '2(C21 H15 N5 O3), 3(C2 H6 O S)'
_chemical_formula_sum            'C48 H48 N10 O9 S3'
_chemical_formula_weight         1005.14
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-04-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-04-29 deposited with the CCDC.	2022-08-24 downloaded from the CCDC.
;
_cell_angle_alpha                62.387(7)
_cell_angle_beta                 72.388(9)
_cell_angle_gamma                73.176(8)
_cell_formula_units_Z            1
_cell_length_a                   8.847(3)
_cell_length_b                   12.275(4)
_cell_length_c                   13.189(4)
_cell_measurement_reflns_used    1431
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      3.61
_cell_volume                     1190.6(7)
_computing_cell_refinement       'SAINT V8.35A (?, 2016)'
_computing_data_reduction        'SAINT V8.35A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9156
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.730
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0627 before and 0.0518 after correction.
The Ratio of minimum to maximum transmission is 0.8489.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       prizm
_exptl_crystal_F_000             526
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4567
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0629
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0785P)^2^+0.8220P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1528
_refine_ls_wR_factor_ref         0.1740
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3267
_reflns_number_total             4567
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj03499a2.cif
_cod_data_source_block           a_a
_cod_depositor_comments          'Adding full bibliography for 7061833.cif.'
_cod_original_cell_volume        1190.7(7)
_cod_database_code               7061833
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S2S_$1-C3S
 1.55 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C3S) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: S2S(0.5) O2S(0.5)
5.a Riding coordinates:
 C3S(H3SA,H3SB,H3SC)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C35(H35), C36(H36), C38(H38), C39(H39),
 C42(H42), C43(H43), C44(H44), C45(H45), C46(H46)
5.c Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C2S(H2SA,H2SB,H2SC)
;
_shelx_res_checksum              36898
_olex2_submission_special_instructions 'No special instructions were received'